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WO2013085339A2 - Organic light-emitting compound and organic electroluminescent device using same - Google Patents

Organic light-emitting compound and organic electroluminescent device using same Download PDF

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WO2013085339A2
WO2013085339A2 PCT/KR2012/010627 KR2012010627W WO2013085339A2 WO 2013085339 A2 WO2013085339 A2 WO 2013085339A2 KR 2012010627 W KR2012010627 W KR 2012010627W WO 2013085339 A2 WO2013085339 A2 WO 2013085339A2
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group
synthesis
mol
inv
formula
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PCT/KR2012/010627
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Korean (ko)
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WO2013085339A3 (en
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김회문
김성무
김영배
김태형
박호철
이창준
백영미
신진용
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주식회사 두산
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Priority claimed from KR20120105048A external-priority patent/KR101488565B1/en
Application filed by 주식회사 두산 filed Critical 주식회사 두산
Priority to US14/363,372 priority Critical patent/US10038146B2/en
Priority to JP2014545825A priority patent/JP5922792B2/en
Publication of WO2013085339A2 publication Critical patent/WO2013085339A2/en
Publication of WO2013085339A3 publication Critical patent/WO2013085339A3/en

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Definitions

  • the present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a novel indole compound having excellent hole injection and transporting ability, light emitting ability and the like, and the light emitting efficiency,
  • the present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting layer forming material of the organic EL device emits blue, green, and red light according to the light emission color It can be divided into materials. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, in order to increase the luminous efficacy through the increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material.
  • the dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of phosphorescent materials can theoretically improve luminous efficiency up to four times that of fluorescence, attracting attention not only for phosphorescent dopants but also phosphorescent host materials.
  • NPB, BCP and Alq 3 rounds represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material.
  • a metal complex compound containing Ir such as Firpic, Ir (ppy) 3l (acac) Ir (btp) 2, etc. is used as a blue, green, and red dopant material.
  • CBP has shown excellent properties as a phosphorescent host material.
  • An object of the present invention is to provide an indole compound and an organic EL device using the same, which can improve driving voltage, luminous efficiency, and the like.
  • the present invention provides a compound represented by the following formula (1).
  • 3 ⁇ 4 and 3 ⁇ 4 are, each independently, hydrogen, deuterium, halogen eu cyano group, a nitro group, C ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, C 6 ⁇ C 60 aryl group, nuclear hetero atoms 5 to 60 heteroaryl group, Cr o alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, C 6 ⁇ C 60 aryl silyl group, C 2 ⁇ C 40 group of an alkyl boron, an aryl boronic of rC 60, C 6 ⁇ C 60 aryl phosphine group, CrCso aryl phosphine oxide group, and a C 6 ⁇ aryl of C 60 Selected from the group consisting of amine groups,
  • Yi to Y4 are each independently N or C3 ⁇ 4, one of Y and ⁇ 2 , ⁇ 2 and ⁇ 3 , or ⁇ 3 and ⁇ 4 forms a condensed ring represented by the following formula (2),
  • ⁇ 5 to ⁇ 8 are each independently N or C, and the dotted line means a site where condensation occurs with the compound of Chemical Formula 1,
  • 3 ⁇ 4 are each independently selected from the group consisting of 0, S, Se, N (An), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein 3 ⁇ 4 and 3 ⁇ 4 At least one is N i ⁇ ), and each of R 3 and R 4 is, independently, hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of Crdo, cycloalkyl group of C 3 ⁇ C 40 , nuclear atom 3 Heterocycloalkyl group of 40 to 40, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of d-do, aryloxy group of rC 60 , alkylsilyl of C 3 -C 40 Group, C 6 ⁇ C 60 arylsilyl group, C 2 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, CrC 60 ary
  • a to Ar 5 each independently, is represented by (: ⁇ (: 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, nucleus Heteroaryl group of 5 to 60 atoms, alkyloxy group of d-o, aryloxy group of 60 , alkylsilyl group of C 3 to C 40 , arylsilyl group of 60 , C 2 to C 40 alkyl boron group, C 6 ⁇ C 6.
  • the arylboronic group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group, and a C 6 ⁇ is selected from the aryl group consisting of an amine group in the C 60 ,
  • the 3 ⁇ 4 to R4 and A to Ar 5 (: ⁇ (: 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, CrCso aryl group, nuclear atom 5 to 60 Heteroaryl group, d ⁇ C 40 alkyloxy group, (: 6 ⁇ (: 60 aryloxy group, C 3 ⁇ C 40 alkylsilyl group, 60 (Arylsilyl group, C 2 ⁇ C 40 Alkyl boron group, rC 60 Aryl boron group, rC 60 Aryl phosphine group, C 6 ⁇ C 60 Aryl phosphine oxide group and C 6 ⁇ C 60 arylamine group, each independently, a deuterium, a halogen, a cyano group, a nitro group, C ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cyclo
  • Y to Y4 are all CR 3
  • 3 ⁇ 4 may be the same or different from each other, and adjacent R 3 may be bonded to each other to form a condensed ring.
  • R 4 may be the same as or different from each other, and adjacent R 4 may be bonded to each other to form a condensed ring.
  • the plurality of substituents may be the same as or different from each other.
  • Alkyl used in the present invention is a straight or cyclic saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl propyl, isobutyl, sec-butyl, pentyl, iso-amyl and nuclear chamber.
  • aryl as used in the present invention means an aromatic moiety having 6 to 60 carbon atoms combined with a single ring or two or more rings, and two or more rings may be attached to each other in a simple or condensed form.
  • aryl include phenyl, indenyl, naphthyl, anthracenyl, fluorenyl, phenanthryl, pyrenyl, chrysenyl dong.
  • heteroaryl used in the present invention means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 60 nuclear atoms, at least one carbon in the ring, preferably 3 to 3 carbons are N, 0, Substituted with a heteroatom such as S, Si or Se.
  • a heteroatom such as S, Si or Se.
  • Such heteroaryl is interpreted to include a form in which two or more rings are simply attached or condensed with each other and further include a condensed form with an aryl group.
  • heteroaryl examples include pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxadizolyl, pyridinyl, pyrimidinyl, triazinyl, carbazolyl, indolyl, quinolinyl, isoqui Nolinil and the like.
  • the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof.
  • the present invention (i) the anode, (ii) the cathode, and (iii) at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is at least one of the formula Provided is an organic electroluminescent device comprising a compound represented by 1 as a tapping agent.
  • the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer.
  • the organic material layer including the compound represented by Formula 1 is a light emitting layer
  • the compound may be used as a phosphorescent host of the light emitting layer.
  • the present invention has a higher molecular weight than the conventional organic electroluminescent device material [Example: 4, 4-di car chili-bi phenyl (hereinafter referred to as CBP)], and has excellent driving voltage characteristics and It provides a new indole-based compound with efficiency.
  • CBP 4-di car chili-bi phenyl
  • Indole compound of the present invention has a structure of a compound represented by the formula (1).
  • the host molecule in order to have a high luminous efficiency, the host molecule should have a higher energy level than the dopant molecule.
  • the compound of the present invention is a condensed carbon ring or a condensed heterocyclic moiety in the indole-based skeleton, preferably The condensed heterocyclic moiety is linked and has a wide bandgap (sky blue to red) by controlling the energy level by various substituents. Therefore, the compound of Chemical Formula 1 may minimize energy loss during the light emission process, and may exhibit an effect of improving the light emission efficiency.
  • these properties of the compound can not only improve the phosphorescence properties of the device, but also improve the hole injection / transport capability, the luminous efficiency, the driving voltage, and the life characteristics.
  • it can be applied to not only the light emitting layer but also the hole transport layer and the electron transport layer.
  • the compound of Formula 1 may exhibit excellent properties as a light emitting host material (blue, green and / or red phosphorescent host material or fluorescent dopant material) compared to the conventional CBP due to the indole moiety.
  • the molecular weight of the compound due to the various aromatic ring (aromatic ring) substituents in the indole-based skeleton, the glass transition temperature is improved, thereby having a higher thermal stability than the conventional CBP. Therefore, the device including the compound of the present invention can be significantly improved durability and life characteristics.
  • Each R 4 independently represents hydrogen, a C 6 to C 60 aryl group (e.g. phenyl, naphthyl, bisphenyl), a heteroaryl group of 5 to 60 nuclear atoms (e.g. pyridine) and a C 6 to C 60 group ; From the group consisting of arylamine groups It is preferably selected, and the C 6 ⁇ C 60 aryl group of 3 ⁇ 4, heteroaryl group of 5 to 60 nuclear atoms and 3 ⁇ 4 ⁇ (: arylamine group of 3 ⁇ 4 ⁇ (: 60 arylamine group is d-o alkyl group, C 6 ⁇ C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.
  • aryl group e.g. phenyl, naphthyl, bisphenyl
  • a heteroaryl group of 5 to 60 nuclear atoms e.g. pyridine
  • aryl group is preferably selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms and an arylamine group of C 6 to C 60 .
  • 3 ⁇ 4 to R 4 and A to Ar 5 may each independently be selected from the following substituent groups (functional groups S1 to S192).
  • the compound represented by the formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the formula la to If.
  • the compounds represented by the general formula (1) of the present invention and 3 ⁇ 4 are both ⁇ .
  • the compound represented by Formula 1 of the present invention may be a compound represented by Formula 3 below.
  • R 2 and ⁇ to Y 4 are as defined above, and ⁇ 2 , ⁇ 2 and ⁇ 3 , or ⁇ 3 and ⁇ 4 increase one to form a condensed ring represented by Formula 4 below. ,.
  • Y 5 to ⁇ 8 are as defined above, and the dotted line means a site where condensation occurs with the compound of Chemical Formula 3, and the Arr (: 6 to (: 60 aryl group or nuclear atom number) and from 5 to 60 heteroaryl group, wherein R a and may be each independently hydrogen eu deuterium, a halogen, a cyano group, a nitro group, an alkyl group of C ⁇ C 40, C 3 ⁇ C 40 cycloalkyl group, the nuclear atoms of 3 to 40; 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, a heteroaryl group of nuclear atoms of 5 to 60, C ⁇ C 40 alkyloxy group, the aryloxy group of the C S ⁇ C 60, ⁇ ( Alkylsilyl group, C 6 ⁇ C 60 Aryl silyl group, C 2 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C ⁇ C
  • heterocycloalkyl groups C 6 to C 60 aryl groups, 5 to 60 nuclear aryl groups, d-o alkyloxy groups, rC 60 aryloxy groups, C 3 to C 40 alkylsilyl groups , C 6 ⁇ C 60 arylsilyl group , c 2 ⁇ c 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, (: 6 ⁇ (: 60 aryl phosphine oxide group and (: 6 ⁇ ( 60
  • the arylamine groups each independently include deuterium, halogen, cyano group, nitro group, alkyl group of CrCio, cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of 60 and nuclear atom A heteroaryl group of 5 to 60 carbon atoms, an alkyloxy group of d to C 40 ,
  • C 2 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C (rC 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group and C 6 ⁇ C 60 arylamine group which may be substituted with one or more substituents selected from the group consisting of n and m, each independently, an integer of 0 to 5, with 111 being at least one.
  • A has the same 2 C 6 ⁇ C 60 aryl group or a nuclear atoms of 5 to 60 hetero arylene groups may be interpreted as the functional groups.
  • R 2 and ⁇ to Y 4 are the same as defined above, and One of Y 2 , Y 2 and VII 3 , or VII 3 and VII 4 forms a condensed ring represented by the following formula (6)
  • X 5 to X 8 are as defined above, and the dotted line means a site where condensation occurs with the compound of Chemical Formula 5, and ⁇ to X 6 are each independently N or CAr 6 .
  • the Ar 6 , A and B each independently, an alkyl group of Cr o, a cycloalkyl group of rC 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 ⁇ C 60 , nuclear number 5 Heteroaryl group of 60 to 60, alkyloxy group of do, aryloxy group of C 6 ⁇ C 60 , alkylsilyl group of C 3 ⁇ C 40 , arylsilyl group of C 6 ⁇ C 60 , C 2 ⁇ C 40 alkyl is selected from boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphine group, C 6 ⁇ C 60 aryl phosphine oxide group
  • the compound represented by Chemical Formula 5 may be selected from the group consisting of compounds represented by the following Chemical Formulas 5a to 5f.
  • the compound represented by the formula (1) of the present invention is 3 ⁇ 4 is N r ⁇ ) when 3 ⁇ 4 is S, 3 ⁇ 4 is ⁇ ⁇ when 3 ⁇ 4 is S! Is preferably.
  • the compound represented by Chemical Formula 1 of the present invention may be selected from the group consisting of compounds represented by the following Chemical Formulas 6a to 61.
  • Yi to Y 8 and A are as defined above.
  • Specific examples of the compound represented by Chemical Formula 1 of the present invention described above include the following compounds (1-1583), but the compound of the present invention is not limited to the following compounds.
  • the compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis process for the compound of Formula 1 of the present invention will be described in detail in the following Examples.
  • the present invention also relates to (i) an anode; (ii) a cathode; And (iii) at least one organic material layer interposed between the anode and the cathode, wherein at least one of the organic material layers comprises at least one compound represented by Chemical Formula 1. It provides an organic electroluminescent device.
  • a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the electron injection layer, the electron transport layer and the light emitting layer may include at least one compound represented by the formula (1).
  • the compound represented by Formula 1 of the present invention can be used as a phosphorescent host of the light emitting layer.
  • the electron injection layer may be positioned on the electron transport layer.
  • an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.
  • the organic material layer including the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing or thermal transfer.
  • the organic electroluminescent device according to the present invention is one of the techniques except that the organic layer is formed to include at least one layer of the compound represented by the formula (1) of the present invention It can be prepared by forming the organic layer and the electrode using materials and methods known in the art.
  • a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, or the like may be used as the substrate.
  • the anode material may be a metal such as vanadium, krum, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium sulfide, indium tin oxide (IT0), indium zinc oxide (IZ0); A combination of a metal and an oxide such as ⁇ : ⁇ 1 or Sn0 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbonblown, and the like, but is not limited thereto.
  • Metal oxides such as zinc oxide, indium sulfide, indium tin oxide (IT0), indium zinc oxide (IZ0); A combination of a metal and an oxide such as ⁇ : ⁇ 1 or Sn0 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used.
  • the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention is not limited by the following examples.
  • ⁇ ⁇ R for IC-lb ⁇ 6.53 (d, IH), 7.27 (d, IH), 7.45 (m, 3H), 7.50 (d, IH), 7.55 (m, 3H), 7.67 (t, IH ), 7.89 (m, 2H), 8.12 (t, IH), 8.25 (s, IH)
  • ⁇ R ⁇ 6.45 (d, IH), 7.26 (d, IH), 7.45 (d, IH), 7.55 (d, IH), 7.64 (d, IH), 7.85 (d, IH), 7.96 (s, IH), 8.13 (s, IH), 8.21 (s, IH)
  • IC-14-1 was obtained by the same procedure as in ⁇ Step 3> of Preparation Example 1.
  • ⁇ ⁇ R ⁇ 6.98 (d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (t ⁇ 2H), 7.46 (m, 6H), 7.58 (d, 1H), 7.81 (d , 4H), 7.87 (m, 4H), 7.93 (d, 1H), 7.99 (d, 1H)
  • a 5- (2-nitrophenyl) -l- (2- (tri was carried out in the same manner as in ⁇ Step 3> of Preparation Example 1, except that 1-l bromo ⁇ 2 ⁇ (tr i fluoromethyl) benzene was used instead of iodobenzene. f luoromethyl) phenyl) -lH-indole was obtained.
  • IC 19-1 obtained in ⁇ Step 1> was used instead of 5- (2-nitr opheny 1) -1-pheny 1 -IH-i ndo 1 e.
  • IC-19 was obtained by performing the same procedure as in the following.
  • IC-la (5 g, 17.71 mmol), 2-br omo-4, 6-di pheny 1 yr idi ne (8.24 g, 26.56 ⁇ l), Cu powder (0.11), which is a compound prepared in Preparation Example 1, under nitrogen stream g'.1.77 mmo 1), 2C0 3 (2.44 g, 17.71 mmol), Na 2 S0 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml) were combined and stirred at 190 ° C for 12 h.
  • IC-6a (5 g, 13.84 ⁇ l), Iodobenzene (4.24 g, 20.76 mmol), Cu powder (0.09 g, 1.38 mmol), K 2 CO 3 (1.91 g, 13.84 dl ol), Na 2 S0 4 (1.97 g, 13.84 mmol) and ni trobenzene (80 ml) were combined and stirred at 190 ° C for 12 h. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 .
  • 6-pheny 1 pyr idi ⁇ -3-y 1 boron ic acidl was used to obtain the title compound Irw-18 (2.63 g, yield 76%).
  • a target compound lnv-28 (2.13 g, 46%) was obtained in the same manner as in Synthesis Example 27, except that 3_ (4 ⁇ bromophenyl) pyridine was used instead of 3-bromobi phenyl.
  • IC-la (3 g, 10.63 ⁇ ol), 2- (3-ch 1 or opheny 1) -4, 6-di heny 1 -1, 3, 5-tri az i ne (4.38 g, 12.75) under nitrogen stream ⁇ ol), Pd (0Ac) 2 (0.12 g, 5 mol%), NaO (t-bu) (2.04 g, 21.25 mmol), P (t ⁇ bu) 3 (0.21 g, 1.06 mmol) and Toluene (100 ml) were combined and stirred at 110 ° C for 12 h.
  • Inv-38 (2.44 g, 44%) was obtained by the same procedure as in Synthesis Example 27, except that (4—bromophenyl) diphenylborane was used instead of 3-bromobi phenyl.
  • Inv-39 (2.59 g , 45%) was prepared in the same manner as in Synthesis Example 27, except that (4-br omopheny 1) di heny 1 phosphine was used instead of 3-bromobi phenyl. Got it.
  • Inv-43 (2.45 g, 53 3 ⁇ 4) was obtained in the same manner as in Synthesis Example 27, except that IC_10a and 3 ⁇ (4 ⁇ bromophenyl) pyridine were used instead of IC ⁇ lb and 3 ⁇ bromobiphenyl. .
  • a target compound lnv-49 (4.69 g, 75) was obtained in the same manner as in Synthesis Example 29, except that IOlOa and 2- (3-chlorophenyl) -4,6-diphenylpyrimidine were used.
  • Inv-51 (3.04 g) was prepared by the same procedure as in Synthesis Example 27, except that 4- (5-br omobi pheny l-3-yl) -2 and 6-di phenyl pyr imidi ne were used. , 43 was obtained.
  • Inv-54 (2.54 g, 44) was obtained in the same manner as in Synthesis Example 27, except that IOlOa and (4-bromophenyl) diphenyl phosphine were used instead of IClb and 3-bromobi henyl.
  • Inv-60 (7.94 g, 69) was prepared in the same manner as in Synthesis Example 59, except that 9-pheny 1 to 9H-car apelo 1-3-y 1 bor on ic acid was used instead of phenylboronic acid. %) was obtained.
  • Inv-78 (2.90 g, 52%) was prepared in the same manner as in Synthesis Example 27, except that 2- (4 ⁇ bromophenyl) -4,6-diphenyl-1,3,5-triazineol was used.
  • Inv-99 (2.25) was prepared in the same manner as in Synthesis Example 27, except that IC ⁇ 28, 1-bromo-3, and 5-diphenyl benzene were used instead of IClb and 3-bromobi henyl. g, 52%).

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Abstract

The present invention relates to a novel indole-based compound having superior hole-injection and -transport capabilities, light-emitting capabilities, and the like, and to an organic electroluminescent device which comprises the indole-based compound in one or more organic layers thereof so as to thereby achieve improved characteristics, such as light-emitting efficiency, driving voltage, and lifespan characteristics.

Description

【명세서】  【Specification】

【발명의 명칭】  [Name of invention]

유기 발광화합물 및 이를 이용한유기 전계 발광 소자  Organic light emitting compound and organic electroluminescent device using same

【기술분야】  Technical Field

본 발명은 신규의 유기 발광 화합물 및 이를 이용한 유기 전계 발광 소자에 관한 것으로， 보다 상세하게는 정공 주입 및 수송능, 발광능 등이 우수한 신규의 인돌계 화합물 및 이를 하나 이상의 유기물층에 포함함으로써 발광효율, 구동 전압, 수명 등의 특성이 향상된 유기 전계 발광 소자에 관한 것이다.  The present invention relates to a novel organic light emitting compound and an organic electroluminescent device using the same, and more particularly, a novel indole compound having excellent hole injection and transporting ability, light emitting ability and the like, and the light emitting efficiency, The present invention relates to an organic EL device having improved characteristics such as driving voltage and lifetime.

【배경기술】  Background Art

1950년대 Bernanose의 유기 박막 발광 관측을 시점으로 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광 (electroluminescent, EL) 소자 (이하， 간단히 '유기 EL 소자'로 칭함)에 대한 연구는 1987년 탕 (Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 EL소자가 제시되었고， 고효율， 고수명의 유기 EL 소자를 만들기 위하여 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어져 왔다.  The study of organic electroluminescent (EL) devices (hereinafter referred to simply as 'organic EL devices') led to blue electroluminescence using anthracene monocrystals in 1965, starting with Bernanose's observation of organic thin film emission in the 1950s. According to (Tang), an organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer has been proposed, and has been developed in the form of introducing each characteristic organic material layer in the device to make a high efficiency and long life organic EL device. It has led to the development of specialized materials used for this.

유기 EL 소자의 두 전극 사이에 전압을 걸어 주면 양극에서는 정공이 주입되고, 음극에서는 전자가유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 액시톤 (exciton)이 형성되며， 이 액시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 유기물층으로사용되는 물질은 기능에 따라， 발광물질， 정공 주입 물질, 정공 수송 물질， 전자 수송 물질， 전자주입 물질 등으로 분류될 수 있다.  When voltage is applied between two electrodes of the organic EL element, holes are injected from the anode, and electrons are injected into the organic organic layer from the cathode. When the injected holes and electrons meet, an exciton is formed, and when the axtone falls to the ground, it shines. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

유기 EL 소자의 발광층 형성재료는 발광색에 따라 청색， 녹색, 적색 발광 재료로 구분될 수 있다. 그밖에, 보다 나은 천연색을 구현하기 위한 발광재료로 노란색 및 주황색 발광재료도사용된다. 또한， 색순도의 중가와 에너지 전이를 통해 발광 효을을 증가시키기 위하여， 발광 재료로서 호스트 /도편트 계를 사용할수 있다. 도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자 (heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 인광 재료의 개발은 이론적으로 형광에 비해 4배까지의 발광 효율을 향상시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트 재료들에 대해 관심이 집증되고 있다. The light emitting layer forming material of the organic EL device emits blue, green, and red light according to the light emission color It can be divided into materials. In addition, yellow and orange light emitting materials are also used as light emitting materials to realize better natural colors. In addition, in order to increase the luminous efficacy through the increase in color purity and energy transfer, a host / dopant system may be used as the light emitting material. The dopant material can be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of phosphorescent materials can theoretically improve luminous efficiency up to four times that of fluorescence, attracting attention not only for phosphorescent dopants but also phosphorescent host materials.

현재까지 정공 수송층. 정공 차단층, 전자 수송층으로는， 하기 화학식으로 표현된 NPB, BCP, Alq3 둥이 널리 알려져 있고， 발광 재료는 안트라센 유도체들이 형광 도판트 /호스트 재료로서 보고되고 있다. 특히 효율 향상 측면에서 큰 장점을 가지고 있는 인광 재료로서는 Firpic, Ir(ppy)3l (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색, 녹색， 적색 도판트 재료로 사용되고 있다. 현재까지는 CBP가 인광호스트 재료로 우수한 특성을 나타내고 있다. Hole transport layer to date. As the hole blocking layer and the electron transporting layer, NPB, BCP and Alq 3 rounds represented by the following chemical formulas are widely known, and anthracene derivatives have been reported as fluorescent dopant / host materials in the light emitting material. In particular, as a phosphorescent material having a great advantage in terms of efficiency improvement, a metal complex compound containing Ir such as Firpic, Ir (ppy) 3l (acac) Ir (btp) 2, etc. is used as a blue, green, and red dopant material. To date, CBP has shown excellent properties as a phosphorescent host material.

Figure imgf000003_0001
Figure imgf000003_0001

그러나 기존의 재료들은 발광 특성 측면에서는 유리한 면이 있으나， 유리전이온도가 낮고 열적 안정.성이 매우 좋지 않아 유기 EL 소자에서의 수명 측면에서 만족할만한 수준이 되지 못하고 있다. However, existing materials have advantages in terms of their luminescence properties, but they have low glass transition temperature and thermal stability. It is not a satisfactory level.

【발명의 상세한 설명】  [Detailed Description of the Invention]

【기술적 과제】  [Technical problem]

본 발명의 목적은 구동전압， 발광효율 등을 향상시킬 수 있는 인돌계 화합물 및 이를 이용한 유기 EL 소자를 제공하는 것이다 .  An object of the present invention is to provide an indole compound and an organic EL device using the same, which can improve driving voltage, luminous efficiency, and the like.

【기술적 해결방법】  Technical Solution

상기 목적을 달성하기 위하여 본 발명은 하기 화학식 1로 표시된 화합물을 제공한다 .  In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

[화학식 1] [Formula 1]

Figure imgf000004_0001
상기 식에서 ¾ 및 ¾는， 각각 독립적으로， 수소， 중수소， 할로겐 ᅳ 시아노기， 니트로기， C广 C40의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 해테로아릴기 , Cr o의 알킬옥시기， C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기， rC60의 아릴보론기， C6~C60의 아릴포스핀기， CrCso의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되고，
Figure imgf000004_0001
Wherein ¾ and ¾ are, each independently, hydrogen, deuterium, halogen eu cyano group, a nitro group, C广C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group of, C 6 ~ C 60 aryl group, nuclear hetero atoms 5 to 60 heteroaryl group, Cr o alkyloxy group, C 6 ~ C 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 aryl silyl group, C 2 ~ C 40 group of an alkyl boron, an aryl boronic of rC 60, C 6 ~ C 60 aryl phosphine group, CrCso aryl phosphine oxide group, and a C 6 ~ aryl of C 60 Selected from the group consisting of amine groups,

상기 Yi 내지 Y4는， 각각 독립적으로， N 또는 C¾이고， Y 과 Υ2 , Υ2와 Υ3 , 또는 γ3와 γ4 중 하나는 하기 화학식 2로 표시되는 축합 고리를 형성하며， Yi to Y4 are each independently N or C¾, one of Y and 과 2 , Υ 2 and Υ 3 , or γ 3 and γ 4 forms a condensed ring represented by the following formula (2),

[화학식 2] [Formula 2]

Figure imgf000005_0001
Figure imgf000005_0001

상기 식에서， γ5 내지 Υ8은, 각각 독립적으로， Ν 또는 C 이고， 점선은 상기 화학샥 1의 화합물과 축합이 이루어지는 부위를 의미하며， In the above formula, γ 5 to Υ 8 are each independently N or C, and the dotted line means a site where condensation occurs with the compound of Chemical Formula 1,

상기 및 ¾는， 각각 독립적으로， 0, S, Se, N(An), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되고, ¾ 및 ¾중 적어도 하나는 N i^)이며， 상기 R3및 R4는,각각독립적으로，수소，중수소, 할로겐， 시아노기， 니트로기， Crdo의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d-do의 알킬옥시기, rC60의 아릴옥시기， C3-C40의 알킬실릴기， C6~C60의 아릴실릴기 , C2~C40의 알킬보론기， C6~C60의 아릴보론기， CrC60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되고， And ¾ are each independently selected from the group consisting of 0, S, Se, N (An), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), wherein ¾ and ¾ At least one is N i ^), and each of R 3 and R 4 is, independently, hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of Crdo, cycloalkyl group of C 3 ~ C 40 , nuclear atom 3 Heterocycloalkyl group of 40 to 40, aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, alkyloxy group of d-do, aryloxy group of rC 60 , alkylsilyl of C 3 -C 40 Group, C 6 ~ C 60 arylsilyl group, C 2 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, CrC 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group And it is selected from the group consisting of C 6 ~ C 60 arylamine group,

상기 A 내지 Ar5는，각각독립적으로， (：广(：40의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d- o의 알킬옥시기， 60의 아릴옥시기， C3~C40의 알킬실릴기, ~(：60의 아릴실릴기， C2~C40의 알킬보론기， C6~C6。의 아릴보론기， C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되며， A to Ar 5 , each independently, is represented by (： 广 (: 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nucleus Heteroaryl group of 5 to 60 atoms, alkyloxy group of d-o, aryloxy group of 60 , alkylsilyl group of C 3 to C 40 , arylsilyl group of 60 , C 2 to C 40 alkyl boron group, C 6 ~ C 6. the arylboronic group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ is selected from the aryl group consisting of an amine group in the C 60 ，

상기 ¾ 내지 R4 및 A 내지 Ar5의 (：广(：40의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기, CrCso의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기， d~C40의 알킬옥시기, (：6~(：60의 아릴옥시기， C3~C40의 알킬실릴기， ~(60의 아릴실릴기, C2~C40의 알킬보론기, rC60의 아릴보론기， rC60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기는， 각각 독립적으로， 중수소， 할로겐， 시아노기， 니트로기， C广 C40의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기， C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6-C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다. The ¾ to R4 and A to Ar 5 (： 广 (: 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, CrCso aryl group, nuclear atom 5 to 60 Heteroaryl group, d ~ C 40 alkyloxy group, (： 6 ~ (： 60 aryloxy group, C 3 ~ C 40 alkylsilyl group, 60 (Arylsilyl group, C 2 ~ C 40 Alkyl boron group, rC 60 Aryl boron group, rC 60 Aryl phosphine group, C 6 ~ C 60 Aryl phosphine oxide group and C 6 ~ C 60 arylamine group, each independently, a deuterium, a halogen, a cyano group, a nitro group, C广C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a nuclear atoms, 3 to 40 hetero cycloalkyl group, C 6 ~ C 60 Aryl group, heteroaryl group having 5 to 60 nuclear atoms, d-C 40 alkyloxy group, C 6 -C 60 aryloxy group, C 3 -C 40 alkylsilyl group, C 6 -C 60 aryl silyl group, C 2 ~ C 40 alkyl group of boron, C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 of the aryl phosphine oxide group, and a C 6 -C It may be substituted with one or more substituents selected from the group consisting of 60 arylamine groups.

여기서,상기 내지 Y4가모두 CR3일 경우 ¾는서로 같거나 다를 수 있으며， 인접한 R3들끼리 결합하여 축합 고리를 형성할수 있다. 또， 상기 Y5 내지 Υ8가모두Herein, when Y to Y4 are all CR 3 , ¾ may be the same or different from each other, and adjacent R 3 may be bonded to each other to form a condensed ring. In addition, all of the Y 5 to Υ 8

CR4일 경우 R4도 서로 같거나 다를 수 있으며， 인접한 R4들끼리 결합하여 축합 고리를 형성할수 있다. In the case of CR 4 , R 4 may be the same as or different from each other, and adjacent R 4 may be bonded to each other to form a condensed ring.

또한， 상기 ¾ 내지 및 A 내지 Ar5가 복수개의 치환기로 치환될 경우， 복수개의 치환기는 서로 같거나 다를 수 있다. In addition, when ¾ to A to Ar 5 are substituted with a plurality of substituents, the plurality of substituents may be the same as or different from each other.

본 발명에서 사용된 알킬은 탄소수 1 내지 40의 직쇄 또는 축쇄의 포화 탄화수소이며,이의 예로는 메틸，에틸 프로필,이소부틸， sec-부틸，펜틸， iso-아밀, 핵실 등올 들 수 있다.  Alkyl used in the present invention is a straight or cyclic saturated hydrocarbon having 1 to 40 carbon atoms, and examples thereof include methyl, ethyl propyl, isobutyl, sec-butyl, pentyl, iso-amyl and nuclear chamber.

또한， 본 발명에서 사용된 아릴은 단독 고리 혹은 2 이상의 고리가 조합된 탄소수 6 내지 60의 방향족 부위를 의미하며， 2 이상의 고리가 서로 단순 부착 (pendant)되거나 축합된 형태로 부착될 수 있다. 이러한 아릴의 예로는 페닐， 인데닐， 나프틸， 안트라세닐， 플루오레닐， 페난트릴， 피레닐, 크리세닐 둥을 들 수 있다. 또， 본 발명에서 사용된 헤테로아릴은 핵원자수 5 내지 60의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 부위를 의미하며， 고리 중 하나 이상의 탄소， 바람직하게는 내지 3개의 탄소가 N, 0, S, Si 또는 Se와 같은 헤테로원자로 치환된다. 이러한 헤테로아릴은 2 이상의 고리가 서로 단순 부착 (pendant)되거나 축합된 형태로 부착될 수 있고， 나아가 아릴기와의 축합된 형태도 포함하는 것으로 해석한다. 헤테로아릴의 예로는 피라졸일， 이미다졸일， 옥사졸일， 티아졸일， 트리아졸일， 테트라졸일， 옥사디아졸일， 피리디닐， 피리미디닐， 트리아지닐, 카바졸일， 인돌일， 퀴놀리닐, 이소퀴놀리닐 등을들수 있다. In addition, aryl as used in the present invention means an aromatic moiety having 6 to 60 carbon atoms combined with a single ring or two or more rings, and two or more rings may be attached to each other in a simple or condensed form. Examples of such aryl include phenyl, indenyl, naphthyl, anthracenyl, fluorenyl, phenanthryl, pyrenyl, chrysenyl dong. In addition, the heteroaryl used in the present invention means a monoheterocyclic or polyheterocyclic aromatic moiety having 5 to 60 nuclear atoms, at least one carbon in the ring, preferably 3 to 3 carbons are N, 0, Substituted with a heteroatom such as S, Si or Se. Such heteroaryl is interpreted to include a form in which two or more rings are simply attached or condensed with each other and further include a condensed form with an aryl group. Examples of heteroaryl include pyrazolyl, imidazolyl, oxazolyl, thiazolyl, triazolyl, tetrazolyl, oxadizolyl, pyridinyl, pyrimidinyl, triazinyl, carbazolyl, indolyl, quinolinyl, isoqui Nolinil and the like.

본 발명에서 사용된 축합 고리는 축합 지방족 고리， 축합 방향족 고리， 축합 헤테로지방족 고리， 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다. 한편， 본 발명은， (i) 양극， (ii) 음극， 및 (iii) 상기 양극과 음극 사이에 개재 (介在)된 1층 이상의 유기물층올 포함하고， 상기 1층 이상의 유기물층 중에서 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것을 톡징으로 하는 유기 전계 발광소자를 제공한다.  As used herein, the condensed ring means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring, or a combination thereof. On the other hand, the present invention, (i) the anode, (ii) the cathode, and (iii) at least one organic layer interposed between the anode and the cathode, at least one of the at least one organic layer is at least one of the formula Provided is an organic electroluminescent device comprising a compound represented by 1 as a tapping agent.

이때, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 정공 주입층， 정공 수송층, 전자 수송층， 전자 주입층 및 발광층으로 구성된 군으로부터 선택될 수 있다.  In this case, the organic material layer including the compound represented by Formula 1 may be selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer and a light emitting layer.

구체적으로， 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층이며, 상기 화합물은상기 발광층의 인광호스트로사용될 수 있다.  Specifically, the organic material layer including the compound represented by Formula 1 is a light emitting layer, the compound may be used as a phosphorescent host of the light emitting layer.

【발명의 실시를 위한 형태】  [Form for implementation of invention]

본 발명은 종래 유기 전계 발광 소자용 재료 [예： 4, 4-di car bazolybi phenyl (이하 CBP로 표시함)]보다 높은 분자량을 가지면서， 우수한 구동 전압 특성과 효율을 갖는 신규의 인돌계 화합물 ( indole— based compound)을 제공한다 . 본 발명의 인돌계 화합물은 상기 화학식 1로 표시된 화합물의 구조를 가진다. The present invention has a higher molecular weight than the conventional organic electroluminescent device material [Example: 4, 4-di car bazolybi phenyl (hereinafter referred to as CBP)], and has excellent driving voltage characteristics and It provides a new indole-based compound with efficiency. Indole compound of the present invention has a structure of a compound represented by the formula (1).

유기 전계 발광 소자에 있어 , 높은 발광 효율을 갖기 위해서는 호스트 분자가 도편트 분자보다 큰 에너지 레벨을 가져야 하는데， 본 발명의 화합물은 인돌계 기본 골격에 축합 탄소고리 또는 축합 해테로환 모이어티， 바람직하게는 축합 헤테로환 모이어티가 연결되고， 여 러 치환체에 의해 에너지 레벨이 조절됨으로써 넓은 밴드갭 (sky blue ~ red)올 갖는다 . 따라서， 상기 화학식 1의 화합물은 발광 과정에서 에너지 손실을 최소화할 수 있어， 발광 효율을 개선시키는 효과를 발휘할 수 있다 . 나아가， 상기 화합물의 이 러한 특성은 소자의 인광 특성올 개선 시킬 수 있을 뿐만 아니라， 정공 주입 /수송 능력， 발광효율 , 구동전압， 수명 특성 등을 개선시킬 수 있다 . 또한, 도입되는 치환체의 종류에 따라 발광층뿐만 아니라 정공 수송층， 전자 수송층 둥에 응용될 수 있다.  In the organic electroluminescent device, in order to have a high luminous efficiency, the host molecule should have a higher energy level than the dopant molecule. The compound of the present invention is a condensed carbon ring or a condensed heterocyclic moiety in the indole-based skeleton, preferably The condensed heterocyclic moiety is linked and has a wide bandgap (sky blue to red) by controlling the energy level by various substituents. Therefore, the compound of Chemical Formula 1 may minimize energy loss during the light emission process, and may exhibit an effect of improving the light emission efficiency. In addition, these properties of the compound can not only improve the phosphorescence properties of the device, but also improve the hole injection / transport capability, the luminous efficiency, the driving voltage, and the life characteristics. In addition, depending on the type of substituents introduced, it can be applied to not only the light emitting layer but also the hole transport layer and the electron transport layer.

특히， 상기 화학식 1의 화합물은 인돌계 모이어티로 인해 종래 CBP에 비해 발광 호스트 재료 (청색， 녹색 및 /또는 적색의 인광 호스트 재료 또는 형광 도편트 재료)로서의 우수한 특성을 나타낼 수 있다. 또한， 인돌계 기본골격에， 다양한 방향족 환 (aromat ic r ing) 치환체로 인해 화합물의 분자량이 유의적으로 증대됨으로써， 유리전이온도가 향상되고 이로 인해 종래 CBP 보다 높은 열적 안정성을 가질 수 있다. 따라서 본 발명의 화합물을 포함하는 소자는 내구성 및 수명 특성 이 크게 향상될 수 있다.  In particular, the compound of Formula 1 may exhibit excellent properties as a light emitting host material (blue, green and / or red phosphorescent host material or fluorescent dopant material) compared to the conventional CBP due to the indole moiety. In addition, the molecular weight of the compound due to the various aromatic ring (aromatic ring) substituents in the indole-based skeleton, the glass transition temperature is improved, thereby having a higher thermal stability than the conventional CBP. Therefore, the device including the compound of the present invention can be significantly improved durability and life characteristics.

여기서， 넓은 bandᅳ gap과 열안정성을 고려했을 때 상기 화학식 1의 ¾ 내지 Here, in consideration of the wide band ᅳ gap and thermal stability,

R4는 각각 독립적으로 수소， C6~C60의 아릴기 (예 : 페닐， 나프틸， 비스페닐 ) , 핵원자수 5 내지 60의 헤테로아릴기 (예 : 피리딘 ) 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 것이 바람직하며, 상기 및 ¾의 C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기 및 ¾~(：60의 아릴아민기는 d- o의 알킬기， C6~C60의 아릴기 및 핵원자수 5 내지 60의 헤테로아릴기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다. Each R 4 independently represents hydrogen, a C 6 to C 60 aryl group (e.g. phenyl, naphthyl, bisphenyl), a heteroaryl group of 5 to 60 nuclear atoms (e.g. pyridine) and a C 6 to C 60 group ; From the group consisting of arylamine groups It is preferably selected, and the C 6 ~ C 60 aryl group of ¾, heteroaryl group of 5 to 60 nuclear atoms and ¾ ~ (: arylamine group of ¾ ~ (: 60 arylamine group is d-o alkyl group, C 6 ~ C 60 It may be substituted with one or more substituents selected from the group consisting of an aryl group and a heteroaryl group having 5 to 60 nuclear atoms.

또한，화학식 1의 ¾및 /또는 ¾가 NCAr , C(Ar2)(Ar3)또는 Si (Ar4)(Ar5)일 때, An 내지 Ar5는， 각각 독립적으로， C6~C60의 아릴기 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 것이 바람직하다. In addition, when ¾ and / or ¾ of Formula 1 is NCAr, C (Ar 2 ) (Ar 3 ) or Si (Ar 4 ) (Ar 5 ), An to Ar 5 are each independently, C 6 ~ C 60 The aryl group is preferably selected from the group consisting of a heteroaryl group having 5 to 60 nuclear atoms and an arylamine group of C 6 to C 60 .

더욱 바람직하게는， ¾ 내지 R4 및 A 내지 Ar5는 각각 독립적으로 하기 치환체 (작용기 S1~S192) 그룹으로부터 선택될 수 있다. More preferably, ¾ to R 4 and A to Ar 5 may each independently be selected from the following substituent groups (functional groups S1 to S192).

Figure imgf000010_0001
Figure imgf000010_0001

Figure imgf000011_0001
Figure imgf000011_0001

LZ90lO/ZlOZ ^/LDd 6££≤80/εΐ0ί OAV LZ90lO / ZlOZ ^ / LDd 6 ££ ≤80 / εΐ0ί OAV

Figure imgf000012_0001
.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV 이러한 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 la 내지 If로 표시되는 화합물로 구성된 군으로부터 선택되는 것 이 바람직하다.
Figure imgf000012_0001
.Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV The compound represented by the formula (1) of the present invention is preferably selected from the group consisting of compounds represented by the formula la to If.

[화학식 la]  [Formula la]

Figure imgf000013_0001
Figure imgf000013_0001

[화학식 lb]  [Formula lb]

Figure imgf000013_0002
Figure imgf000013_0002

[화학식 lc]  [Formula lc]

Figure imgf000013_0003
Figure imgf000013_0003

[화학식 Id]  Formula Id

Figure imgf000013_0004
Figure imgf000013_0004

[화학식 le] [Formula le]

Figure imgf000014_0001
Figure imgf000014_0001

[화학식 if] [Formula if]

Figure imgf000014_0002
Figure imgf000014_0002

상기 화학식 la내지 If에서， ， R2, Xi, ¾및 내지 ^은 상기에서 정의한 바와같다. In formulas la to If, R 2 , Xi, ¾ and to ^ are as defined above.

또한, 유기 전계 발광 소자의 구동전압 및 전류효율올 고려할 때， 본 발명의 화학식 1로 표시되는 화합물은 및 ¾가 모두 ^^^인 것이 바람직하다. 구체적으로， 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 3으로 표시되는 화합물일 수 있다.  In addition, considering the driving voltage and current efficiency of the organic electroluminescent device, it is preferable that the compounds represented by the general formula (1) of the present invention and ¾ are both ^^^. Specifically, the compound represented by Formula 1 of the present invention may be a compound represented by Formula 3 below.

[화학식 3]

Figure imgf000014_0003
상기 화학식 3에서， ， R2및 ^내지 Y4는상기에서 정의한 바와 같으며 , 과 Υ2, Υ2와 Υ3, 또는 Υ3와 Υ4 증 하나는 하기 화학식 4로 표시되는 축합 고리를 형성하며， . [Formula 3]
Figure imgf000014_0003
In Formula 3, R 2 and ^ to Y 4 are as defined above, and 과 2 , Υ 2 and Υ 3 , or Υ 3 and Υ 4 increase one to form a condensed ring represented by Formula 4 below. ，.

[화학식 4]  [Formula 4]

Figure imgf000015_0001
Figure imgf000015_0001

상기 화학식 4에서， Y5내지 Υ8은 상기에서 정의한 바와 같으며, 점선은상기 화학식 3의 화합물과 축합이 이루어지는 부위를 의미하고， 상기 Arr (：6~(：60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이고， 상기 Ra 및 는 각각 독립적으로 수소ᅳ 중수소, 할로겐, 시아노기， 니트로기， C广 C40의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， C广 C40의 알킬옥시기, CS~C60의 아릴옥시기， ~(；40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기 , C6~C60의 아릴보론기， C6~C60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선텍되몌 In Chemical Formula 4, Y 5 to Υ 8 are as defined above, and the dotted line means a site where condensation occurs with the compound of Chemical Formula 3, and the Arr (： 6 to (： 60 aryl group or nuclear atom number) and from 5 to 60 heteroaryl group, wherein R a and may be each independently hydrogen eu deuterium, a halogen, a cyano group, a nitro group, an alkyl group of C广C 40, C 3 ~ C 40 cycloalkyl group, the nuclear atoms of 3 to 40; 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, a heteroaryl group of nuclear atoms of 5 to 60, C广C 40 alkyloxy group, the aryloxy group of the C S ~ C 60, ~ ( Alkylsilyl group, C 6 ~ C 60 Aryl silyl group, C 2 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphine group, C 6 ~ C 60 Selected from the group consisting of an aryl phosphine oxide group and an arylamine group of C 6 ~ C 60

상기 Ra 및 ¾의 Cr o의 알킬기， C3~C40의 시클로알킬기, 핵원자수 3 내지The R a and ¾ Cr o alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 to

40의 헤테로시클로알킬기, C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d- o의 알킬옥시기， rC60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， c2~c40의 알킬보론기， C6~C60의 아릴보론기 , C6~C60의 아릴포스핀기， (：6~(：60의 아릴포스핀옥사이드기 및 (：6~( 60의 아릴아민기는， 각각 독립적으로 , 중수소 , 할로겐， 시아노기， 니트로기， CrCio의 알킬기 , C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기， 60의 아릴기， 핵원자수 5 내지 60의 해테로아릴기， d~C40의 알킬옥시기， C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C6。의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기， C(rC60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있으며， 상기 n 및 m은， 각각 독립적으로， 0 내지 5의 정수이고， 단 111은 적어도 1 이상이다 . 여기서， 상기 화학식 3의 구조를 볼 때， A 은 C6~C60의 아릴렌기 또는 핵원자수 5 내지 60의 헤테로아릴렌기와 같은 2가 작용기로 해석될 수도 있다. 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 nuclear aryl groups, d-o alkyloxy groups, rC 60 aryloxy groups, C 3 to C 40 alkylsilyl groups , C 6 ~ C 60 arylsilyl group ， c 2 ~ c 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, (： 6 ~ (： 60 aryl phosphine oxide group and (： 6 ~ ( 60 The arylamine groups each independently include deuterium, halogen, cyano group, nitro group, alkyl group of CrCio, cycloalkyl group of C 3 to C 40 , heterocycloalkyl group of 3 to 40 nuclear atoms, aryl group of 60 and nuclear atom A heteroaryl group of 5 to 60 carbon atoms, an alkyloxy group of d to C 40 , an aryloxy group of C 6 to C 60 , an alkylsilyl group of C 3 to C 40 , an arylsilyl group of C 6 to C 6 . C 2 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C (rC 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and C 6 ~ C 60 arylamine group Which may be substituted with one or more substituents selected from the group consisting of n and m, each independently, an integer of 0 to 5, with 111 being at least one. When viewing the structure of a group the formula 3, A has the same 2 C 6 ~ C 60 aryl group or a nuclear atoms of 5 to 60 hetero arylene groups may be interpreted as the functional groups.

더욱 바람직하게는 , 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 More preferably, the compound represented by Formula 1 of the present invention is

5로 표시되는 화합물일 수 있다. It may be a compound represented by 5.

[화학식 5]  [Formula 5]

Figure imgf000016_0001
상기 화학식 5에서 , ， R2 및 ^ 내지 Y4는 상기에서 정의한 바와 같으며 , ^과 Y2, Y2와 Υ3, 또는 Υ3와 Υ4 중 하나는 하기 화학식 6으로 표시되는 축합 고리를 형성하고
Figure imgf000016_0001
In Chemical Formula 5, R 2 and ^ to Y 4 are the same as defined above, and One of Y 2 , Y 2 and VII 3 , or VII 3 and VII 4 forms a condensed ring represented by the following formula (6)

[화학식 6]  [Formula 6]

Figure imgf000017_0001
Figure imgf000017_0001

상기 화학식 6에서, Υ5내지 丫8은 상기에서 정의한 바와 같으며， 점선은상기 화학식 5의 화합물과 축합이 이루어지는 부위를 의미하고， 상기 Λ 내지 Ζ6은， 각각 독립적으로， Ν또는 CAr6이며，상기 Ar6, A및 B는，각각 독립적으로, Cr o의 알킬기 , rC40의 시클로알킬기， 핵원자수 3 내지 40의 해테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기, d o의 알킬옥시기, C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기， C6~C60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되고, 상기 r 및 s는 각각 0 내지 5의 정수이고， 단 r+s는 적어도 1 이상이며， 상기 p 및 q는 각각 0 내지 3의 정수이다. In Chemical Formula 6, X 5 to X 8 are as defined above, and the dotted line means a site where condensation occurs with the compound of Chemical Formula 5, and Λ to X 6 are each independently N or CAr 6 . ， The Ar 6 , A and B, each independently, an alkyl group of Cr o, a cycloalkyl group of rC 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 ~ C 60 , nuclear number 5 Heteroaryl group of 60 to 60, alkyloxy group of do, aryloxy group of C 6 ~ C 60 , alkylsilyl group of C 3 ~ C 40 , arylsilyl group of C 6 ~ C 60 , C 2 ~ C 40 alkyl is selected from boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group, and a C 6 ~ C 60 aryl group consisting of amine group for the a, R and s are each an integer of 0 to 5, except that r + s is at least 1, and p and q are each an integer of 0 to 3, respectively.

이때， 상기 화학식 5로 표시되는 화합물은 하기 화학식 5a 내지 5f로 표시되는 화합물로 구성된 군으로부터 선택될 수 있다.  In this case, the compound represented by Chemical Formula 5 may be selected from the group consisting of compounds represented by the following Chemical Formulas 5a to 5f.

[화학식 5a] [Formula 5a]

Figure imgf000018_0001
Figure imgf000018_0001

[화학식 5b]

Figure imgf000018_0002
[Formula 5b]
Figure imgf000018_0002

[화학식 5c]

Figure imgf000018_0003
[Formula 5c]
Figure imgf000018_0003

[화학식 5d] [Formula 5d]

Figure imgf000019_0001
Figure imgf000019_0001

[화학식 5e]

Figure imgf000019_0002
[Formula 5e]
Figure imgf000019_0002

[화학식 5Π [Formula 5Π

Figure imgf000020_0001
상기 화학식 5a내지 5ί에서, Ri, R2, Y:내지 Υ8, Ζι내지 Z6, A, B, r, s, p및 q는 상기에서 정의한 바와 같다.
Figure imgf000020_0001
In Formulas 5a to 5ί, Ri, R 2 , Y: to Υ 8 , Ζι to Z 6 , A, B, r, s, p, and q are as defined above.

또한, 상기 화학식 5로 표시되는 화합물의 Ar6, A 및 B는， 각각 독립적으로， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 것이 바람직하다. In addition, Ar 6 , A and B of the compound represented by Formula 5, each independently, a C 6 ~ C 60 aryl group, a nuclear atom of 5 to 60 heteroaryl group and C 6 ~ C 60 arylamine It is preferably selected from the group consisting of groups.

한편， 유기 전계 발광 소자의 구동전압 및 전류효율을 고려할 때， 본 발명의 화학식 1로 표시되는 화합물은 ¾이 S일 때 ¾는 N r^)이고, ¾가 S일 때 ¾는 ^八 ；！인 것이 바람직하다. 구체적으로， 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 6a 내지 61로 표시되는 화합물로 구성된 군으로부터 선택될 수 있다. On the other hand, considering the driving voltage and current efficiency of the organic electroluminescent device, the compound represented by the formula (1) of the present invention is ¾ is N r ^) when ¾ is S, ¾ is ^ 八 when ¾ is S! Is preferably. Specifically, the compound represented by Chemical Formula 1 of the present invention may be selected from the group consisting of compounds represented by the following Chemical Formulas 6a to 61.

[화학식 6a]  [Formula 6a]

Figure imgf000020_0002
Figure imgf000020_0002

[화학식 6b] [Formula 6b]

Figure imgf000021_0001
Figure imgf000021_0001

[화학식 6c]

Figure imgf000021_0002
[Formula 6c]
Figure imgf000021_0002

[화학식 6e]

Figure imgf000021_0003
[Formula 6e]
Figure imgf000021_0003

[화학식 6f] [Formula 6f]

Figure imgf000022_0001
Figure imgf000022_0001

[화학식 6h]

Figure imgf000022_0002
[Formula 6h]
Figure imgf000022_0002

[화학식 6j] [Formula 6j]

Figure imgf000023_0001
상기 식에서， ， ， Yi 내지 Y8 및 A 은상기에서 정의한바와 같다. 이상에서 설명한 본 발명의 화학식 1로 표시되는 화합물의 구체적인 예로, 하기 화합물들 (1-1583)을 들 수 있지만， 본 발명의 화합물이 하기 화합물들로 한정되는 것은 아니다.
Figure imgf000023_0001
In the above formula, ， Yi to Y 8 and A are as defined above. Specific examples of the compound represented by Chemical Formula 1 of the present invention described above include the following compounds (1-1583), but the compound of the present invention is not limited to the following compounds.

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.Z90l0 / ZT0ZaM / X3d 6CCS80 / CT0Z OAV

Figure imgf000061_0001
Figure imgf000061_0001

6CCS80/i:iOZ; OAV 6CCS80 / i: iOZ; OAV

Figure imgf000062_0001
Figure imgf000062_0001

.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV .Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000063_0001
Figure imgf000063_0001

.Z90lO/ZTOZaM/X3d 6CCS80/CT0Z OAV .Z90lO / ZTOZaM / X3d 6CCS80 / CT0Z OAV

Figure imgf000064_0001
Figure imgf000064_0001

Ζ.Ζ90ΐΟ/ΖΙΟΖΗΜ/Χ3«Ι Ζ.Ζ90ΐΟ / ΖΙΟΖΗΜ / Χ3 «Ι

Figure imgf000065_0001
Figure imgf000065_0001

/.Ζ90ΪΟ/ΖϊθεΗ¾/Χ3<ΐ /.Ζ90ΪΟ/ΖϊθεΗ¾/Χ3 < ΐ

6iTS80/no∑: OAV 6iTS80 / no∑: OAV

Figure imgf000066_0001
Figure imgf000066_0001

6ecs80eioz OAV6ecs80eioz OAV

LI90lO/ZlOIHH/I3d LI90lO / ZlOIHH / I3d

Figure imgf000067_0001
.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV
Figure imgf000067_0001
.Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000068_0001
Figure imgf000068_0001

.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV .Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000069_0001
Figure imgf000069_0001

.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV .Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000070_0001
Figure imgf000070_0001

.Ζ90ΐΟ/ΖΐΟΖΗΜ/Χ3<Ι 6CCS80/CT0Z OAV .Ζ90ΐΟ / ΖΐΟΖΗΜ / Χ3 <Ι 6CCS80 / CT0Z OAV

Figure imgf000071_0001
.Ζ90ΐΟ/ΖΪΟΖΗΜ/Χ3<Ι 6CCS80/CT0Z OAV
Figure imgf000071_0001
.Ζ90ΐΟ / ΖΪΟΖΗΜ / Χ3 <Ι 6CCS80 / CT0Z OAV

Figure imgf000072_0001
Figure imgf000072_0001

6££S80/£10Z ΟΛ 6 ££ S80 / £ 10Z ΟΛ

Figure imgf000073_0001
Figure imgf000073_0001

.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV .Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000074_0001
.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV
Figure imgf000074_0001
.Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000075_0001
Figure imgf000075_0001

6ees80/eioi OAV .Ζ90ΙΟ/ΖΐΟΖ)Γ»/Ι3Λ 6ees80 / eioi OAV .Ζ90ΙΟ / ΖΐΟΖ) Γ »/ Ι3Λ

Figure imgf000076_0001
Figure imgf000076_0001

.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV .Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000077_0001
Figure imgf000077_0001

.Z90lO/ZTOZaM/X3d 6CCS80/CT0Z OAV

Figure imgf000078_0001
.Z90lO/ZTOZaM/X3d 6CCS80/CT0Z OAV
Figure imgf000079_0001
.Z90lO / ZTOZaM / X3d 6CCS80 / CT0Z OAV
Figure imgf000078_0001
.Z90lO / ZTOZaM / X3d 6CCS80 / CT0Z OAV
Figure imgf000079_0001

Figure imgf000080_0001
z.z90io/zioraM/x3d 6CCS80/£10∑; OAV
Figure imgf000081_0001
.Z90l0/ZT0ZaM/X3d 6CCS80/CT0Z OAV
Figure imgf000080_0001
z. z90io / zioraM / x3d 6CCS80 / £ 10∑; OAV
Figure imgf000081_0001
.Z90l0 / ZT0ZaM / X3d 6CCS80 / CT0Z OAV

Figure imgf000082_0001
.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV
Figure imgf000082_0001
.Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV

Figure imgf000083_0001
.Ζ90ΐ0/ΖΪ0ΖΗΜ/Χ3<1 6CCS80/CT0Z OAV 본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다. 본 발명의 화학식 1의 화합물에 대한 상세한 합성 과정은 후술하는 실시예에서 구체적으로 기술하도록 한다.
Figure imgf000083_0001
.Ζ90ΐ0 / ΖΪ0ΖΗΜ / Χ3 <1 6CCS80 / CT0Z OAV The compound of formula 1 of the present invention may be synthesized according to a general synthetic method. Detailed synthesis process for the compound of Formula 1 of the present invention will be described in detail in the following Examples.

본 발명은 또한 (i) 양극 (anode); (ii) 음극 (cathode); 및 (iii) 상기 양극과 음극 사이에 개재 (介在)된 1충 이상의 유기물층을 포함하는 유기 전계 발광 소자로서， 상기 유기물층 중 적어도 하나는상기 화학식 1로 표시되는 화합물을 1종 이상포함하는 것을 특징으로 하는 유기 전계 발광 소자를 제공한다.  The present invention also relates to (i) an anode; (ii) a cathode; And (iii) at least one organic material layer interposed between the anode and the cathode, wherein at least one of the organic material layers comprises at least one compound represented by Chemical Formula 1. It provides an organic electroluminescent device.

본 발명에 따른 유기 전계 발광 소자 구조의 비제한적인 예를 들면, 기판， 양극， 정공 주입층, 정공 수송층， 발광층， 전자수송층 및 음극이 순차적으로 적층된 것일 수 있다. 이때 정공 주입층， 정공 수송층, 전자주입층， 전자수송층 및 발광층 중 하나 이상은 상기 화학식 1로 표시되는 화합물을 1종 이상포함할 수 있다. 또한 본 발명의 화학식 1로 표시되는 화합물은 발광층의 인광 호스트로 이용될 수 있다. 상기 전자수송층 위에는 전자주입층이 위치할수도 있다.  As a non-limiting example of the organic electroluminescent device structure according to the present invention, a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode may be sequentially stacked. In this case, at least one of the hole injection layer, the hole transport layer, the electron injection layer, the electron transport layer and the light emitting layer may include at least one compound represented by the formula (1). In addition, the compound represented by Formula 1 of the present invention can be used as a phosphorescent host of the light emitting layer. The electron injection layer may be positioned on the electron transport layer.

또한， 본 발명에 따른 유기 전계 발광 소자는 전술한 바와 같이 양극， 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라， 전극과 유기물층 계면에 절연층 또는 접착층이 삽입될 수 있다.  In addition, in the organic electroluminescent device according to the present invention, as described above, not only a structure in which an anode, at least one organic material layer, and a cathode are sequentially stacked, an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.

본 발명에 따른 유기 전계 발광 소자에 있어서， 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는스핀 코팅， 딥코팅， 닥터 블레이딩， 잉크젯 프린팅 또는 열 전사법 등이 있으나， 이들에만 한정되지 않는다.  In the organic electroluminescent device according to the present invention, the organic material layer including the compound represented by Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing or thermal transfer.

본 발명에 따른 유기 전계 발광 소자는 유기물층 중 1층 이상을 본 발명의 화학식 1로 표시되는 화합물올 포함하도록 형성하는 것을 제외하고는 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다. The organic electroluminescent device according to the present invention is one of the techniques except that the organic layer is formed to include at least one layer of the compound represented by the formula (1) of the present invention It can be prepared by forming the organic layer and the electrode using materials and methods known in the art.

예컨대， 기판으로는 실리콘 웨이퍼， 석영 또는 유리판, 금속판， 폴라스틱 필름이나 시트 등이 사용될 수 있다.  For example, a silicon wafer, a quartz or glass plate, a metal plate, a plastic film or sheet, or the like may be used as the substrate.

양극 물질로는 바나듐， 크룸， 구리， 아연， 금과 같은 금속 또는 이들의 합금; 아연산화물， 인듐샅화물, 인듐 주석 산화물 (IT0), 인듐 아연 산화물 (IZ0)과 같은 금속 산화물; ΖηΟ:Α1 또는 Sn02:Sb와 같은 금속과 산화물의 조합; 폴리티오펜， 폴리 (3-메틸티오펜), 폴리 [3,4- (에틸렌 -1，2-디옥시)티오펜] (PEDT), 폴리피를 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블택 등이 있으나， 이들에만 한정되는 것은 아니다. The anode material may be a metal such as vanadium, krum, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium sulfide, indium tin oxide (IT0), indium zinc oxide (IZ0); A combination of a metal and an oxide such as ΖηΟ: Α1 or Sn0 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbonblown, and the like, but is not limited thereto.

음극 물질로는 마그네슘， 칼슘， 나트륨, 칼륨， 타이타늄， 인듐， 이트륨, 리튬, 가돌리늄， 알투미늄, 은， 주석， 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02/Al과 같은 다층 구조 물질 등이 있으나， 이들에만 한정되는 것은 아니다. The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.

또한， 정공 주입층， 정공 수송층， 전자 주입층 및 전자 수송층은 특별히 한정되는 것은 아니며， 당업계에 알려진 통상의 물질이 사용될 수 있다. 이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단， 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.  In addition, the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, conventional materials known in the art may be used. Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention is not limited by the following examples.

[준비예 1] IC-la및 IC-lb의 합성 Preparation Example 1 Synthesis of IC-la and IC-lb

<단계 1> 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)— lH-indole의

Figure imgf000086_0001
<Step 1> 5- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) — of lH-indole
Figure imgf000086_0001

질소 기류 하에서 5-bromo-lH- indole (25 g, 0.128 mol), 4,4,4' A' ,5,5, 5' ,5'-octamethyl-2,2'-bi(l,3,2-(iioxaborolane) (48.58 g, 0.191 mol), Pd(dppf)Cl2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) 및 DMF (500 ml)를 흔합하고 130°C에서 12시간동안교반하였다. 5-bromo-lH-indole (25 g, 0.128 mol), 4,4,4 'A', 5,5, 5 ', 5'-octamethyl-2,2'-bi (l, 3, Mix 2- (iioxaborolane) (48.58 g, 0.191 mol), Pd (dppf) Cl 2 (5.2 g, 5 mol), KOAc (37.55 g, 0.383 mol) and DMF (500 ml) and 12 hours at 130 ° C Stir for a while.

반응이 종결된 후 에틸아세테이트로 추출한 다음 MgS04로 수분을 제거하고， 컬럼크로마토그래피 (Hexane:EA 10:1 (v/v))로 정제하여After completion of the reaction, the mixture was extracted with ethyl acetate, followed by removal of water with MgS0 4 , and purification by column chromatography (Hexane: EA 10: 1 (v / v)).

5-(414,5,5-tetramethyl-l)3,2-dioxaborolan-2-yl)-lH-indole (12.43 g,수율 40%)을 얻었다. 5- (4 1 4,5,5-tetramethyl-l ) 3,2-dioxaborolan-2-yl) -H-indole (12.43 g, yield 40%) was obtained.

¾-NMR: δ 1.24 (s, 12H), 6.45 (d, 1H) , 7.27 (d, 1H) , 7.42 (d, 1H) , 7.52 (d, ¾-NMR: δ 1.24 (s, 12H), 6.45 (d, 1H), 7.27 (d, 1H), 7.42 (d, 1H), 7.52 (d,

1H), 7.95 (s, 1H), 8.21 (s, 1H) 1H), 7.95 (s, 1H), 8.21 (s, 1H)

<단계 2> 5-(2-nitrophenyl)-lH-indole의 합성  <Step 2> Synthesis of 5- (2-nitrophenyl) -lH-indole

Figure imgf000086_0002
Figure imgf000086_0002

질소 기류 하에서 l-bromo-2-nitrobenzene (8 g, 39.6 mmol), 상기 <단계 L-bromo-2-nitrobenzene (8 g, 39.6 mmol) under a stream of nitrogen, said <step

1>에서 얻은 5-(4,4)5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole (11.55 g, 47.5 mmol), NaOH (4.75 g, 118.8 mmol) 및 THF/H20(200 ml/100 ml)를 혼합한 다음，5- (4,4 ) 5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -H-indole (11.55 g, 47.5 mmol) obtained from 1>, NaOH (4.75 g, 118.8 mmol) and Mix THF / H 2 0 (200 ml / 100 ml),

40°C에서 Pd(PPh3)4(2.29 g, 5 mol)를 넣고 80°C에서 12시간동안 교반하였다. 반웅 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:EA = 3:1 (v/v))로 정제하여 5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e (6.5 g, 수율 69%)을 얻었다.Pd (PPh 3 ) 4 (2.29 g, 5 mol) was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of reaction, the mixture was extracted with methylene chloride and MgS0 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give 5- (2-nitr opheny 1)-1H- i ndo 1 e (6.5 g, 69% yield). )

—丽 R: δ 6.47 (d, 1H), 7.25 (d, 1H) , 7.44 (d, 1H)' 7.53 (d, 1H) , 7.65 (t, 1H), 7.86 (t, 1H), 7.95 (s, 1H), 8.00 (d, 1H), 8.09 (t, 1H), 8.20 (s, 1H) — 丽 R: δ 6.47 (d, 1H), 7.25 (d, 1H), 7.44 (d, 1H) ' 7.53 (d, 1H), 7.65 (t, 1H), 7.86 (t, 1H), 7.95 (s , 1H), 8.00 (d, 1H), 8.09 (t, 1H), 8.20 (s, 1H)

<단계 3> 5-(2-nitrophenyl)-l—phenyl-lH-indole의 합성  <Step 3> Synthesis of 5- (2-nitrophenyl) -l—phenyl-lH-indole

Figure imgf000087_0001
Figure imgf000087_0001

nitrobenzene  nitrobenzene

질소 기류 하에서 상기 <단계 2>에서 얻은 5-(2-nitrophenyl)-lH-indoIe (6.5 g, 27.28 mmol), lodobenzene (8.35 g, 40.93 mmol), Cu powder (0.17 g, 2.73 mmol), 2C03 (3.77 g, 27.28 mmol), Na2S0 (3.88 g, 27.28 mmol), nitrobenzene (100 ml)를 흔합하고 19CTC에서 12시간동안교반하였다. 5- (2-nitrophenyl) -lH-indoIe (6.5 g, 27.28 mmol), lodobenzene (8.35 g, 40.93 mmol), Cu powder (0.17 g, 2.73 mmol) obtained in the above <Step 2> under nitrogen stream, 2 C0 3 (3.77 g, 27.28 mmol), Na 2 S0 (3.88 g, 27.28 mmol) and nitrobenzene (100 ml) were combined and stirred at 19 CTC for 12 hours.

반응 종결 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리하여 MgS04를 사용하여 물올 제거하였다. 물이 제거된 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:MC = 3:1 (v/v))로 정제하여 5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e (6.7 g, 수율 78%)올 얻었다.After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 . The solvent was removed from the organic layer, where the water was removed, and then purified by column chromatography (Hexane: MC = 3: 1 (v / v)) to obtain 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e (6.7 g, yield 78%) was obtained.

-賺: δ 6.48 (d, 1H), 7.26 (d, 1H), 7.45 (m, 3H) , 7.55 (m, 4H) , 7.63 (t, 1H), 7.84 (t, 1H), 7.93 (s, 1H)， 8.01 (d, 1H), 8.11 (t, 1H)  賺: δ 6.48 (d, 1H), 7.26 (d, 1H), 7.45 (m, 3H), 7.55 (m, 4H), 7.63 (t, 1H), 7.84 (t, 1H), 7.93 (s, 1H), 8.01 (d, 1H), 8.11 (t, 1H)

<단계 4> la 및 IC-lb의 합성

Figure imgf000088_0001
얻은Step 4 Synthesis of la and IC-lb
Figure imgf000088_0001
Obtained

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e (6 g, 19.09 mmol), t r i heny 1 hosph i ne ( PPh3 )5- (2-nitr opheny 1)-1-pheny 1-IH- i ndo 1 e (6 g, 19.09 mmol), tri heny 1 hosph i ne (PPh 3 )

(12.52 g, 47.72 mmol) 및 1,2-dichlorobenzene (50 ml)를 혼합하고 12시간 동안 교반하였다. (12.52 g, 47.72 mmol) and 1,2-dichlorobenzene (50 ml) were mixed and stirred for 12 hours.

반응 종료 후 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 얻어진 유기층에 대해 MgS04로 물을 제거하고， 컬럼크로마토그래피 (Hexane:MC=3:l (v/v))로 정제하여 IC-la (2.32 g,수율 43¾>)와 IC~lb (2.21 gᅳ수율 41%)을 얻었다. After the reaction was completed, 1,2-dichlorobenzene was removed and extracted with dichloromethane. Water was removed using MgS0 4 with respect to the obtained organic layer, and purified by column chromatography (Hexane: MC = 3: l (v / v)) to obtain IC-la (2.32 g, yield 43¾>) and IC to lb (2.21 g). Yield 41%) was obtained.

IOla에 대한1 H-NMR: δ 6.51 (d, IH) , 7.28 (d, IH) , 7.46 (m, 3H) , 7.51 (s, IH), 7.56 (m, 3H)， 7.64 (t, IH), 7.85 (m, 2H) , 8.08 (t, IH), 8.24 (s, IH) 1 H-NMR for IOla: δ 6.51 (d, IH), 7.28 (d, IH), 7.46 (m, 3H), 7.51 (s, IH), 7.56 (m, 3H), 7.64 (t, IH) , 7.85 (m, 2H), 8.08 (t, IH), 8.24 (s, IH)

IC-lb에 대한 ᅳ丽 R: δ 6.53 (d, IH), 7.27 (d, IH), 7.45 (m, 3H), 7.50 (d, IH), 7.55 (m, 3H) , 7.67 (t, IH), 7.89 (m, 2H), 8.12 (t, IH), 8.25 (s, IH)  ᅳ 丽 R for IC-lb: δ 6.53 (d, IH), 7.27 (d, IH), 7.45 (m, 3H), 7.50 (d, IH), 7.55 (m, 3H), 7.67 (t, IH ), 7.89 (m, 2H), 8.12 (t, IH), 8.25 (s, IH)

[준비예 2] IC-2의 합성  Preparation Example 2 Synthesis of IC-2

<단계 1> 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole의  <Step 1> of 4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indole

Figure imgf000088_0002
5-bromo-lH- indole 대신 4-bromo-lH- indole를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 1>과 동일한 과정올 수행하여 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indoIe을 얻었다.
Figure imgf000088_0002
Except for using 4-bromo-lH- indole instead of 5-bromo-lH- indole to perform the same process as in <Step 1> of Preparation Example 1 4- (4,4,5,5-tetramethyl- l, 3,2-dioxaborolan-2-yl) -lH-indoIe was obtained.

¾ NMR: δ 1.26 (s, 12H), 6.43 (d, 1H) , 7.26 (t, 1H), 7.48 (d, 1H), 7.74 (d, 1H), 7.85 (d, 1H), 8.23 (s, 1H)  ¾ NMR: δ 1.26 (s, 12H), 6.43 (d, 1H), 7.26 (t, 1H), 7.48 (d, 1H), 7.74 (d, 1H), 7.85 (d, 1H), 8.23 (s, 1H)

<단계 2> 4-(2-nitrophenyl)-lH-indole의 합성  <Step 2> Synthesis of 4- (2-nitrophenyl) -lH-indole

Figure imgf000089_0001
Figure imgf000089_0001

5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole 대신 상기 <단계 1>에서 얻은 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>와 동일한 과정을 수행하여 4- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e을 얻었다.  4- (4,4,5,5-tetramethyl- obtained in <Step 1> instead of 5- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -H-indole Except for using l, 3,2-dioxaborolan-2-yl) -lH-indole, the same procedure as in <Step 2> of Preparation Example 1 was carried out to provide 4- (2-nitr opheny 1) -1H- i ndo 1 e was obtained.

¾匪 R: δ 6.45 (d, 1H), 7.27 (t, 1H)， 7.50 (d, 1H), 7.66 (t, 1H)， 7.75 (d, 1H), 7.89 (m, 2H), 7.99 (d, 1H), 8.04 (d, 1H), 8.24 (s, 1H)  ¾ 匪 R: δ 6.45 (d, 1H), 7.27 (t, 1H), 7.50 (d, 1H), 7.66 (t, 1H), 7.75 (d, 1H), 7.89 (m, 2H), 7.99 (d , 1H), 8.04 (d, 1H), 8.24 (s, 1H)

<단계 3> 4-(2-nitrophenyl)-l— phenyl-lH-indole의 합성  Step 3 Synthesis of 4- (2-nitrophenyl) -l—phenyl-lH-indole

Figure imgf000089_0002
Figure imgf000089_0002

nitrobenzene  nitrobenzene

5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e 대신 상기 <단계 2>에서 얻은 4-(2-nitrophenyl)-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을수행하여 4-(2-nitrophenyl)-l— phenyl-lH-indole을 얻었다. <Step 3 of Preparation Example 1>, except that 4- (2-nitrophenyl) -lH-indole obtained in <Step 2> was used instead of 5- (2-nitr opheny 1)-1H-i ndo 1 e. and The same procedure was followed to obtain 4- (2-nitrophenyl) -l— phenyl-lH-indole.

¾丽 R: δ 6.47 (d, 1H), 7.28 (t, 1H), 7.47 (m, 2H), 7.52 (m, 2H), 7.60 (m, 2H), 7.67 (t, 1H), 7.75 (d, 1H), 7.89 (m, 2H), 8.00 (d, 1H), 8.06 (d, 1H)  ¾ 丽 R: δ 6.47 (d, 1H), 7.28 (t, 1H), 7.47 (m, 2H), 7.52 (m, 2H), 7.60 (m, 2H), 7.67 (t, 1H), 7.75 (d , 1H), 7.89 (m, 2H), 8.00 (d, 1H), 8.06 (d, 1H)

<단계 4> IC-2의 합성

Figure imgf000090_0001
Step 4 Synthesis of IC-2
Figure imgf000090_0001

5-(2-ni trophenyl )-l-phenyl-lH- indole 대신 상기 <단계 3>에서 얻은 4-(2-nitrophenyl)-l-phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한 과정을 수행하여 IC-2을 얻었다.  Except for using 4- (2-nitrophenyl) -l-phenyl-lH-indole obtained in <Step 3> instead of 5- (2-ni trophenyl) -l-phenyl-lH-indole of Preparation Example 1 IC-2 was obtained by following the same procedure as in <Step 4>.

¾匪 R: δ 6.49 (d, 1H), 7.29 (t, 1H), 7.46 (m, 2H), 7.54 Cm, 2H), 7.61 (d, 1H), 7.69 (t, 1H), 7.74 (d, 1H), 7.88 (m, 2H) , 8.01 (d, 1H), 8.04 (d, 1H), 8.23 ¾ 匪 R: δ 6.49 (d, 1H), 7.29 (t, 1H), 7.46 (m, 2H), 7.54 Cm, 2H), 7.61 (d, 1H), 7.69 (t, 1H), 7.74 (d, 1H), 7.88 (m, 2H), 8.01 (d, 1H), 8.04 (d, 1H), 8.23

(s, 1H) (s, 1H)

[준비예 3] IC-3의 합성  Preparation Example 3 Synthesis of IC-3

〈단계 1> 7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole의 합성  <Step 1> Synthesis of 7- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indole

Figure imgf000090_0002
Figure imgf000090_0002

5-bromo-lH- indole 대신 7-bromo-lH-indole를 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 한 과정을 수행하여 Except for using 7-bromo-lH-indole instead of 5-bromo-lH-indole, perform the same procedure as in <Step 1> of Preparation Example 1

7-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole을 얻었다. ¾ 應 R: δ 1.25 (s, 12H), 6.43 (d, 1H), 7.25 (d, 1H), 7.45 (t, 1H) , 7.56 (d, 1H), 7.71 (d, 1H), 8.22 (s, 1H) 7- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indole was obtained. ¾ 應 R: δ 1.25 (s, 12H), 6.43 (d, 1H), 7.25 (d, 1H), 7.45 (t, 1H), 7.56 (d, 1H), 7.71 (d, 1H), 8.22 (s , 1H)

<단계 2> 7— (2-nitrophenyl)-lH-indole의 합성  <Step 2> 7— Synthesis of (2-nitrophenyl) -lH-indole

Figure imgf000091_0001
Figure imgf000091_0001

5-(4,4,5,5-tetramethyl-l,3,2 -d i oxaborol an-2-y 1 ) - 1Hᅳ i ndo 1 e

Figure imgf000091_0002
5- (4,4,5,5-tetramethyl-l, 3,2 -di oxaborol an-2-y 1)-1H ᅳ i ndo 1 e
Figure imgf000091_0002

<단계 1>에서 얻은 7-(4，4，5，5ᅱ: etramethyl-l,3,2-dioxaborolan-2-yl)-lH— indole을 사용하는 것올 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 7-(2-nitrophenyl)-lH-indole을 얻었다.  7- (4, 4, 5, 5 5: etramethyl-l, 3,2-dioxaborolan-2-yl) -lH— obtained in <Step 1> except that using indole <Step 2 of Preparation Example 1 > The same procedure as in to obtain 7- (2-nitrophenyl) -lH-indole.

¾醒 R: δ 6.42 (d, 1H), 7.24 (d, 1H), 7.43 (t, 1H), 7.55 (d, 1H), 7.70 (m, 2H), 7.88 (t, 1H), 8.01 (d, 1H), 8.11 (d, 1H), 8.23 (s, 1H)  ¾ 醒 R: δ 6.42 (d, 1H), 7.24 (d, 1H), 7.43 (t, 1H), 7.55 (d, 1H), 7.70 (m, 2H), 7.88 (t, 1H), 8.01 (d , 1H), 8.11 (d, 1H), 8.23 (s, 1H)

<단계 3>그 (2-nitn)phenyl)-l—phenyl-lH-indole의 합성  <Step 3> Synthesis of (2-nitn) phenyl) -l—phenyl-lH-indole

Figure imgf000091_0003
Figure imgf000091_0003

5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e 대신 상기 <단계 2>에서 얻은 그 (2-nitrophenyl )-1Η- indole을 사용하는 것올 제외하고는 준비예 1의 <단계 3>과 동일한과정올수행하여 7-(2-nitrophenyl)-l-phenyl-lH-indole을 얻었다.  Except for using (2-nitrophenyl) -1Η- indole obtained in <Step 2> instead of 5- (2-nitr opheny 1)-1H-i ndo 1 e <Step 3> of Preparation Example 1 The same procedure was followed to obtain 7- (2-nitrophenyl) -l-phenyl-lH-indole.

¾ NMR: δ 6.43 (d, 1H), 7.26 (d, 1H) , 7.44 (m, 3H) , 7.56 (m, 4H), 7.71 (m, 2H), 7.89 (t, 1H), 8.02 (d, 1H), 8.10 (d, 1H) <단계 4> IC-3의 합성 ¾ NMR: δ 6.43 (d, 1H), 7.26 (d, 1H), 7.44 (m, 3H), 7.56 (m, 4H), 7.71 (m, 2H), 7.89 (t, 1H), 8.02 (d, 1H), 8.10 (d, 1H) Step 4 Synthesis of IC-3

Figure imgf000092_0001
Figure imgf000092_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 3>에서 얻은 7-(2— nitrophenyl)-l-phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한과정을수행하여 IC-3을 얻었다.  Except for using 7- (2—nitrophenyl) -l-phenyl-lH-indole obtained in <Step 3> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H-i ndo 1 e Performed the same procedure as in <Step 4> of Preparation Example 1 to obtain IC-3.

匪 R: δ 6.45 (d, 1H), 7.24 (d, 1H)， 7.45 (m, 3H) , 7.57 (m, 3H), 7.63 (d, 1H), 7.70 (d, 1H), 7.88 (t, 1H), 8.00 (d, 1H), 8.09 (d, 1H)， 8.22 (s, 1H)  匪 R: δ 6.45 (d, 1H), 7.24 (d, 1H), 7.45 (m, 3H), 7.57 (m, 3H), 7.63 (d, 1H), 7.70 (d, 1H), 7.88 (t, 1H), 8.00 (d, 1H), 8.09 (d, 1H), 8.22 (s, 1H)

[준비예 4] IC-4a및 IC-4b의 합성  Preparation Example 4 Synthesis of IC-4a and IC-4b

<단계 1> 5-(l-nitronaphthalen-2-yl)-lH-indole의 합성  <Step 1> Synthesis of 5- (l-nitronaphthalen-2-yl) -lH-indole

Figure imgf000092_0002
Figure imgf000092_0002

l-bromo-2-ni trobenzene 대신 2ᅳ bromoᅳ l_ni tronaphthalene을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 5-(l-nitronaphthal en-2-y 1 ) -1H- i ndo 1 e을 얻었다. Except for using 2 ᅳ bromo ᅳ l_ni tronaphthalene instead of l-bromo-2-ni trobenzene, the same process as in <Step 2> of Preparation Example 1 was carried out to obtain 5- (l-nitronaphthal en-2-y 1)- 1H-i ndo 1 e was obtained.

NMR: δ 6.44 (d, 1H), 7.26 (d, 1H), 7.43 (d, 1H), 7.53 (d, 1H), 7.64 (m, 3H), 7.80 (πι' 3H), 7.94 (s, 1H), 8.23 (s, 1H)  NMR: δ 6.44 (d, 1H), 7.26 (d, 1H), 7.43 (d, 1H), 7.53 (d, 1H), 7.64 (m, 3H), 7.80 (πι '3H), 7.94 (s, 1H ), 8.23 (s, 1H)

<단계 2> 5-(l-nitronaphthalen-2-yl)-l-phenyl-lH-indole의 합성

Figure imgf000093_0001
<Step 2> Synthesis of 5- (l-nitronaphthalen-2-yl) -l-phenyl-lH-indole
Figure imgf000093_0001

nitrobenzene  nitrobenzene

5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 5-(l-nitronaphthalen-2-yl)-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 5-(l-nitronaphthalen-2-yl)-l-phenyl— LH-indole을 얻었다.  Preparation Example 1 except for using 5- (l-nitronaphthalen-2-yl) -lH-indole obtained in <Step 1> instead of 5- (2-nitr opheny 1)-IH- i ndo 1 e The same procedure as in <Step 3> was performed to obtain 5- (l-nitronaphthalen-2-yl) -l-phenyl—LH-indole.

¾ NMR: δ 6.44 (d, IH), 7.26 (d, IH)， 7.43 (m, 3H) , 7.53 (m, 4H)ᅳ 7.64 (m, 3H), 7.80 (m, 3H), 7.94 (s, IH)  ¾ NMR: δ 6.44 (d, IH), 7.26 (d, IH), 7.43 (m, 3H), 7.53 (m, 4H) ᅳ 7.64 (m, 3H), 7.80 (m, 3H), 7.94 (s, IH)

<단계 3> IC-4a 및 IC— 4b의 합성  Step 3 Synthesis of IC-4a and IC-4b

Figure imgf000093_0002
Figure imgf000093_0002

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 2>에서 얻은 5- (2-n i t r opheny 1)-1-pheny 1-IH- i ndo 1 e instead of <Step 2>

5-(l-nitronaphthalen-2-yl)-l— phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한과정을수행하여 IC-4a와 IC-4b를 얻었다. Except for using 5- (l-nitronaphthalen-2-yl) -l—phenyl-lH-indole, the same procedure as in <Step 4> of Preparation Example 1 was performed to obtain IC-4a and IC-4b.

ICᅳ 4a에 대한 ¾-NMR: δ 6.44 (d, IH), 7.26 (m, 2H) , 7.43 (s, IH) , 7.53 (m, 4H), 7.64 On, 3H)， 7.71 (s, IH), 7.80 (m, 3H), 8.20 (s, IH)  ¾-NMR for IC 4a: δ 6.44 (d, IH), 7.26 (m, 2H), 7.43 (s, IH), 7.53 (m, 4H), 7.64 On, 3H), 7.71 (s, IH) , 7.80 (m, 3H), 8.20 (s, IH)

ICᅳ 4b에 대한 -醒 R: δ 6.43 (d, IH), 7.27 (m, 2H), 7.42 (d, IH), 7.55 (m, -醒 R for IC '4b: δ 6.43 (d, IH), 7.27 (m, 2H), 7.42 (d, IH), 7.55 (m,

4H), 7.65 (d, IH), 7.72 (m, 3H) , 7.82 (m, 3H), 8.20 (s, IH) [준비예 5] IC-5a및 IC-5b의 합성 4H), 7.65 (d, IH), 7.72 (m, 3H), 7.82 (m, 3H), 8.20 (s, IH) Preparation Example 5 Synthesis of IC-5a and IC-5b

<단계 1> 5-(2-nitronaphthalen-l-yl)-lH-indole의 합성  <Step 1> Synthesis of 5- (2-nitronaphthalen-l-yl) -lH-indole

Figure imgf000094_0001
Figure imgf000094_0001

l-bromo-2-ni trobenzene 대신 l—bromo一 2一 nitronaphthalene을 사용하는 것올 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 5- ( 2-n i t r onaph t ha 1 en- 1-y 1 ) - IH- i ndo 1 e을 얻었다.  Except for using l—bromo 一 2 一 nitronaphthalene instead of l-bromo-2-ni trobenzene, the same procedure as in <Step 2> of Preparation Example 1 was carried out to obtain 5- (2-nitr onaph t ha 1 en- 1 -y 1) -IH-i ndo 1 e was obtained.

:H NMR: δ 6.43 (d, IH), 7.25 (d, IH), 7.44 (d, IH), 7.55 (d, IH), 7.67 (m, 2H), 7.81 (d, IH), 7.96 (m, 2H), 8.00 (d, IH), 8.05(d, IH), 8.23 (s, IH) : H NMR: δ 6.43 (d , IH), 7.25 (d, IH), 7.44 (d, IH), 7.55 (d, IH), 7.67 (m, 2H), 7.81 (d, IH), 7.96 (m , 2H), 8.00 (d, IH), 8.05 (d, IH), 8.23 (s, IH)

<단계 2> 5-(2-nitronaphthalen-l-yl)-l- phenyl-lH-indole의 합성  <Step 2> Synthesis of 5- (2-nitronaphthalen-l-yl) -l-phenyl-lH-indole

Figure imgf000094_0002
Figure imgf000094_0002

5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 5-(2-^ 0031 ^31«1ᅳ1ᅳ 0-111-01(1016을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 5- (2-nitr opheny 1)-5- (2- ^ 0031 ^ 31 «1 ᅳ 1 ᅳ 0-111-01 (1016) obtained in <Step 1> instead of IH- i ndo 1 e except And the same process as in <Step 3> of Preparation Example 1

5- ( 2-n i t r onaph t ha 1 en- 1-y 1 ) -1-pheny 1-lH-indole을 얻었다. 5- (2-n i t r onaph t ha 1 en- 1-y 1) -1-pheny 1-lH-indole was obtained.

¾ NMR: δ 6.45 (d, IH), 7.26 (d, IH) , 7.45 (m, 2H), 7.54 (m, 2H), 7.66 (m, 3H), 7.80 (d, IH), 7.96 (m, 2H), 8.01 (m, 2H), 8.06 (m, 2H)  ¾ NMR: δ 6.45 (d, IH), 7.26 (d, IH), 7.45 (m, 2H), 7.54 (m, 2H), 7.66 (m, 3H), 7.80 (d, IH), 7.96 (m, 2H), 8.01 (m, 2H), 8.06 (m, 2H)

<단계 3> IC-5a 및 IC-5b의 합성

Figure imgf000095_0001
Step 3 Synthesis of IC-5a and IC-5b
Figure imgf000095_0001

IC-5b  IC-5b

5-(2-ni trophenyl )-l-phenyl-lH- indole 대신 상기 <단계 2>에서 얻은 5-(2-nitronaphthalen-l-yl)-l-phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한 과정을 수행하여 IC-5a와 IC-5b를 얻었다. Except for using 5- (2-nitronaphthalen-l-yl) -l-phenyl-lH-indole obtained in <Step 2> instead of 5- (2-ni trophenyl) -l-phenyl-lH-indole IC-5a and IC-5b were obtained by performing the same procedure as in <Step 4> of Preparation Example 1.

IC-5a에 대한1 Hᅳ丽 R: δ 6.45 (d, IH), 7.26 (d, IH) , 7.45 (s, IH)， 7.54 (s, IH), 7.66 (m, 2H)， 7.80 (ra, 3H), 7.96 (m, 2H), 8.01 (m, 2H), 8.06 (m, 2H), 8.21 (s, IH) 1 H ᅳ 丽 R for IC-5a: δ 6.45 (d, IH), 7.26 (d, IH), 7.45 (s, IH), 7.54 (s, IH), 7.66 (m, 2H), 7.80 (ra , 3H), 7.96 (m, 2H), 8.01 (m, 2H), 8.06 (m, 2H), 8.21 (s, IH)

IC-5b에 대한 ¾-NMR: δ 6.43 (d, IH), 7.25 (d, IH), 7.46 (d, IH), 7.57 (d, IH), 7.65 (m, 2H), 7.81 (m, 3H), 7.95 (m, 2H), 8.00 (m, 2H)， 8.05 (m, 2H), 8.21 (s, IH)  ¾-NMR for IC-5b: δ 6.43 (d, IH), 7.25 (d, IH), 7.46 (d, IH), 7.57 (d, IH), 7.65 (m, 2H), 7.81 (m, 3H ), 7.95 (m, 2H), 8.00 (m, 2H), 8.05 (m, 2H), 8.21 (s, IH)

[준비예 6] IC-6a및 IC-6b의 합성  Preparation Example 6 Synthesis of IC-6a and IC-6b

<단계 1> 5-(5-bronx)-2-ni trophenyl )-lH-indole의 합성  <Step 1> Synthesis of 5- (5-bronx) -2-ni trophenyl) -lH-indole

Figure imgf000095_0002
Figure imgf000095_0002

l-brorao-2-ni trobenzene 대신 2 ,4—di bromo— 1一 nitrobenzene을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정올 수행하여 5- ( 5-bromo-2-n i t r opheny 1 )ᅳ IH一 i ndo 1 e을 얻었다. Instead of l-brorao-2-ni trobenzene, 2,4—di bromo— 1 一 nitrobenzene should be used. Except for <Step 2> of Preparation Example 1, except that 5- (5-bromo-2-nitr opheny 1) ᅳ IH1 i ndo 1 e was obtained.

醒 R: δ 6.45 (d, IH), 7.26 (d, IH), 7.45 (d, IH) , 7.55 (d, IH), 7.64 (d, IH), 7.85 (d, IH), 7.96 (s, IH), 8.13 (s, IH) , 8.21 (s, IH)  醒 R: δ 6.45 (d, IH), 7.26 (d, IH), 7.45 (d, IH), 7.55 (d, IH), 7.64 (d, IH), 7.85 (d, IH), 7.96 (s, IH), 8.13 (s, IH), 8.21 (s, IH)

<단계 2> 5-(5-bromo-2-nitrophenyl)-l-phenyl-lH-indole의 합성  <Step 2> Synthesis of 5- (5-bromo-2-nitrophenyl) -l-phenyl-lH-indole

Figure imgf000096_0001
Figure imgf000096_0001

5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 5- ( 5-br omo-2-η i t r opheny 1 ) - IH- i ndo 1 e 을 사용하는 것올 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 5-(5-bromo-2-ni trophenyl )- 1-pheny 1-lH-i ndo le 얻었다.  Using 5- (5-br omo-2-η itr opheny 1)-IH- i ndo 1 e obtained in <Step 1> instead of 5- (2-nitr opheny 1)-IH- i ndo 1 e Except for the same procedure as in <Step 3> of Preparation Example 1 except that 5- (5-bromo-2-ni trophenyl) -1-pheny 1-lH-i ndo le was obtained.

¾ NMR: δ 6.44 (d, IH), 7.25 (d, IH) , 7.46 (m, 3H) , 7.56 (m, 4H) , 7.65 (d, IH), 7.86 (d, IH), 7.95 (s, IH), 8.11 (s, IH)  ¾ NMR: δ 6.44 (d, IH), 7.25 (d, IH), 7.46 (m, 3H), 7.56 (m, 4H), 7.65 (d, IH), 7.86 (d, IH), 7.95 (s, IH), 8.11 (s, IH)

<단계 3> IC-6a 및 IC-6b의 합성  Step 3 Synthesis of IC-6a and IC-6b

Figure imgf000096_0002
Figure imgf000096_0002

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 2>에서 얻은 5-(5-bromo-2-nitrophenyl)-lᅳ phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한 과정을 수행하여 IC-6a과 IC-6b를 얻었다. 5- (2-nitr opheny 1)-1-pheny 1-IH- i ndo 1 e obtained in <Step 2> instead of Except for using 5- (5-bromo-2-nitrophenyl) -l phenyl-lH-indole was carried out the same procedure as in <Step 4> of Preparation Example 1 to obtain IC-6a and IC-6b .

IC-6a에 대한1 H-NMR: δ 6.44 (d, IH), 7.25 (d, IH) , 7.39 (m, 2H), 7.46 (s, IH), 7.50 (s, IH), 7.58 (m, 3H) , 7.65 (d, IH), 7.86 (d, IH), 8.11 (s, IH), 8.22 (s, IH) 1 H-NMR for IC-6a: δ 6.44 (d, IH), 7.25 (d, IH), 7.39 (m, 2H), 7.46 (s, IH), 7.50 (s, IH), 7.58 (m, 3H), 7.65 (d, IH), 7.86 (d, IH), 8.11 (s, IH), 8.22 (s, IH)

ICᅳ 6b에 대한 XH-NMR: δ 6.45 (d, IH) , 7.26 (d, IH), 7.38 (m, 2H), 7.45 (d, IH), 7.51 (d, IH), 7.57 On, 3H), 7.64 (d, IH), 7.85 (d, IH), 8.10 (s, IH), 8.23 (s, IH) X H-NMR for IC ᅳ 6b: δ 6.45 (d, IH), 7.26 (d, IH), 7.38 (m, 2H), 7.45 (d, IH), 7.51 (d, IH), 7.57 On, 3H ), 7.64 (d, IH), 7.85 (d, IH), 8.10 (s, IH), 8.23 (s, IH)

[준비예 7] IC-7의 합성  Preparation Example 7 Synthesis of IC-7

<단계 1> 1- (4, 6-diphenylpyr idin-2-yO-4-( 2-ni trophenyl )~LH- indole의 합성 '  <Step 1> Synthesis of 1- (4, 6-diphenylpyr idin-2-yO-4- (2-ni trophenyl) ~ LH-indole ''

Figure imgf000097_0001
Figure imgf000097_0001

5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 4-(2-ni trophenyl )-lH-indole을 사용하고 Iodobenzene 대신 2-brom으 4,6-diphenylpyr idine을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 5- (2-nitr opheny 1)-except that 4- (2-ni trophenyl) -lH-indole is used instead of IH- i ndo 1 e and 4,6-diphenylpyr idine is 2-brom instead of Iodobenzene Performs the same process as in <Step 3> of Preparation Example 1

1- ( 4， 6ᅳ d i pheny lpyridi η-2-y】 ) -4ᅳ ( 2-n i tr opheny 1 ) - IH— i ndo 1 e을 얻었다ᅳ 1- (4 ， 6 ᅳ d i pheny lpyridi η-2-y]) -4 ᅳ (2-n i tr opheny 1)-IH— i ndo 1 e was obtained

GC-Mass (이론치 : 467.16 g/mol, 측정치 : 467 g/mol)  GC-Mass (Theoretical value: 467.16 g / mol, Measured value: 467 g / mol)

<단계 2> IC-7의 합성 Step 2 Synthesis of IC-7

Figure imgf000098_0001
Figure imgf000098_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 1- ( 4， 6-d i pheny lpyr idin-2-yl )-4-(2-ni tr opheny 1 ) - 1H- i ndo 1 e을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한과정을 수행하여 IC-7을 얻었다.  1- (4, 6-di pheny lpyr idin-2-yl) -4- (2 obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e IC-7 was obtained by the same procedure as in <Step 4> of Preparation Example 1, except that -ni tr opheny 1) -1H-i ndo 1 e was used.

GC-Mass (이론치 : 435.17 g/mol, 측정치: 435 g/mol)  GC-Mass (Theoretical value: 435.17 g / mol, Measured value: 435 g / mol)

[준비예 8] IC-8의 합성  Preparation Example 8 Synthesis of IC-8

<단계 1> l-(4,6-di pheny lpyridi η-2-y 1 ) -7- ( 2-ni t r opheny 1 )— 1H- i ndo 1 e의  <Step 1> l- (4,6-di pheny lpyridi η-2-y 1) -7- (2-ni t r opheny 1) — of 1H- i ndo 1 e

Figure imgf000098_0002
Figure imgf000098_0002

5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e 대신 그 (2-nitrophenyl )-lH-indole을 사용하고 5- (2-n i t r opheny 1)-1H- i ndo 1 e instead of (2-nitrophenyl) -lH-indole

Iodobenzene 대신 2—bromo—4,6—di pheny I pyridine을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여Except for using 2—bromo—4,6—di pheny I pyridine instead of iodobenzene, the same procedure as in <Step 3> of Preparation Example 1 was performed.

1- ( 4， 6-d i pheny 1 pyr i d i η-2-y 1 ) -7- ( 2-n i t r opheny 1 )— 1H- i ndo 1 e을 얻었다. 1- (4, 6-d i pheny 1 pyr i d i η-2-y 1) -7- (2-n i t r opheny 1) — 1H- i ndo 1 e was obtained.

GC-Mass (이론치: 467.16 g/mol, 측정치: 467 g/mol)  GC-Mass (Theoretical value: 467.16 g / mol, Measured value: 467 g / mol)

<단계 2> IC-8의 합성 Step 2 Synthesis of IC-8

Figure imgf000099_0001
Figure imgf000099_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 l-(4,6-di pheny lpyridi η-2-y l)-7-(2-nitr opheny 1 )ᅳ 1H- i ndo 1 e을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한 과정을 수행하여 IC-8을 얻었다.  L- (4,6-di pheny lpyridi η-2-yl) -7- (2 obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e IC-8 was obtained by the same procedure as in <Step 4> of Preparation Example 1, except that -nitr opheny 1) ᅳ 1H-i ndo 1 e was used.

GC-Mass (이론치 : 435.17 g/mol , 측정치 : 435 g/mol)  GC-Mass (Theoretical value: 435.17 g / mol, Measured value: 435 g / mol)

[준비예 9] IC-9의 합성  Preparation Example 9 Synthesis of IC-9

<단계 1> l-(2,3'-bipyridin-6-yl)-4-(2-nitrophenyl)-lH-indole의 합성  <Step 1> Synthesis of l- (2,3'-bipyridin-6-yl) -4- (2-nitrophenyl) -lH-indole

Figure imgf000099_0002
Figure imgf000099_0002

nitrobenzene  nitrobenzene

Iodobenzene 대신 6ᅳ bromo一 2,3'一 bipyr idine을 사용하는 것  Using 6 ᅳ bromo 一 2,3 '一 bipyr idine instead of iodobenzene

준비예 2의 <단계 3>과 동일한 과정을

Figure imgf000099_0003
The same process as in <Step 3> of Preparation Example 2
Figure imgf000099_0003

1-(2，3 ' -bipyr idin-6-yl)-4-(2-nitrophenyl)-lH— indole을 얻었다. 1- (2,3'-bipyr idin-6-yl) -4- (2-nitrophenyl) -lH-indole was obtained.

GC-Mass (이론치: 392.13 g/mol, 측정치: 392 g/mol)  GC-Mass (Theoretical value: 392.13 g / mol, Measured value: 392 g / mol)

<단계 2> IC-9의 합성  Step 2 Synthesis of IC-9

Figure imgf000099_0004
5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 1ᅳ (2,3'-bipyridin-6-yl)-4-(2—nitrophenyl)-lH-indole을 사용하는 것을 제외하고는 <단계 4>와동일한과정을 수행하여 IC-9를 얻었다.
Figure imgf000099_0004
1 ((2,3'-bipyridin-6-yl) -4- (2—nitrophenyl) obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H-i ndo 1 e Except for using) -lH-indole, IC-9 was obtained by following the same procedure as in <Step 4>.

GC-Mass (이론치 : 360.14 g/mol, 측정치: 360 g/mol)  GC-Mass (Theoretical value: 360.14 g / mol, Measured value: 360 g / mol)

[준비예 10] IC-10a및 IC-10b의 합성  Preparation Example 10 Synthesis of IC-10a and IC-10b

<단계 1> 6-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl )-1Η— indole의  <Step 1> 6- (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl) -1Η— of indole

Figure imgf000100_0001
Figure imgf000100_0001

5-bromo-lH-indole 대신 6-bromo-lH-indole를 사용하는 것을 제외하고 상기 준비예 1의 <단계 1>과 동일한 과정을 수행하여 Except for using 6-bromo-lH-indole instead of 5-bromo-lH-indole by performing the same process as in <Step 1> of Preparation Example 1

6-(4,4，5， 5-tetramethyl-l, 3 ,2-dioxaborolan-2-yl)-lH-indole을 얻었다. 6- (4,4,5, 5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -H-indole was obtained.

ᅳ丽: δ 1.25 (s, 12H), 6.52 (d, 1H), 7.16 (d, 110， 7.21 (d, 1H), 7.49 (d, 1H), 7.53 (s, 1H), 8.15 (s, 1H)  ᅳ 丽: δ 1.25 (s, 12H), 6.52 (d, 1H), 7.16 (d, 110, 7.21 (d, 1H), 7.49 (d, 1H), 7.53 (s, 1H), 8.15 (s, 1H )

<단계 2> 6-(2-nitrophenyl)-lH-indole의 합성  Step 2 Synthesis of 6- (2-nitrophenyl) -lH-indole

Figure imgf000100_0002
Figure imgf000100_0002

5-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl)-lH-indole 대신 5- (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl) -lH-indole instead

6-(4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl ) 1Hᅳ indol 사용하는 것을 제외하고는 상기 준비예 1의 <단계 2>과 동일한 과정을 수행하여 6-(2-nit r opheny 1 ) - IH- i ndo 1 e을 얻었다. 6- (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl) 1H ᅳ indol Except for the same process as in <Step 2> of Preparation Example 1 except 6- (2-nit r opheny 1)-IH- i ndo 1 e was obtained.

^-NMR: δ 6.57 (d, IH), 7.07 (d, IH), 7.24 (d, IH) , 7.35 (s, IH) , 7.43 (t, IH), 7.50 (d, IH), 7.58 (t, IH), 7.66 (d, IH), 7.78 (d, IH), 8.19 (s, IH)  ^ -NMR: δ 6.57 (d, IH), 7.07 (d, IH), 7.24 (d, IH), 7.35 (s, IH), 7.43 (t, IH), 7.50 (d, IH), 7.58 (t , IH), 7.66 (d, IH), 7.78 (d, IH), 8.19 (s, IH)

<단계 3> 6-(2-nitrophenyl)-l-phenyl-lH-indole의 합성  Step 3 Synthesis of 6- (2-nitrophenyl) -l-phenyl-lH-indole

Figure imgf000101_0001
Figure imgf000101_0001

nitrobenzene  nitrobenzene

5- ( 2-n i t r opheny 1 ) -IH- i ndo 1 e 대신 6-(2_ni trophenyl )-lH-indole를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 6-(2-ni trophenyl )-l-phenyl-lH-indole을. 얻었다. Except for using 6- (2_ni trophenyl) -lH-indole instead of 5- (2-nitr opheny 1) -IH- i ndo 1 e was prepared in the same manner as in <Step 3> of Preparation Example 6 -(2-ni trophenyl) -l-phenyl-lH-indole . Got it.

¾-NMR: 6 6.81 (d, IH), 7.12 (t, IH), 7.22 (t, IH)， 7.35 (s, IH)， 7.43 (d, IH), 7.51 (m, 3H), 7.56 (m, 2H), 7.62 (m, 2H), 7.85 (d, IH), 8.02 (d, IH)  ¾-NMR: 6 6.81 (d, IH), 7.12 (t, IH), 7.22 (t, IH), 7.35 (s, IH), 7.43 (d, IH), 7.51 (m, 3H), 7.56 (m , 2H), 7.62 (m, 2H), 7.85 (d, IH), 8.02 (d, IH)

<단계 4> IC-lOa 및 IC-lOb의 합성  Step 4 Synthesis of IC-lOa and IC-lOb

Figure imgf000101_0002
Figure imgf000101_0002

5-(2-ni trophenyl ) - 1-pheny 1 - IH- i ndo 1 e 대신 6-(2-ni trophenyl )-l-phenyl-lH-indole를 사용하는 것올 제외하고는 상기 준비예 1의 <단계 4>과동일한과정을 수행하여 IC-lOa 및 IC-lOb을 얻었다. 5- (2-ni trophenyl)-1-pheny 1-IH- i ndo 1 e instead Except for using 6- (2-ni trophenyl) -l-phenyl-lH-indole was carried out the same procedure as in <Step 4> of Preparation Example 1 to obtain IC-1Oa and IC-1Ob.

¾-NMR: δ 6.80 (d, 1H), 7.11 (t, 1H), 7.23 (t, 1H), 7.42 (d, 1H) , 7.50 (m, 3H), 7.57 (m, 2H), 7.63 (m, 2H), 7.86 (d, 1H), 8.03 (d, 1H), 9.81 (s, 1H)  ¾-NMR: δ 6.80 (d, 1H), 7.11 (t, 1H), 7.23 (t, 1H), 7.42 (d, 1H), 7.50 (m, 3H), 7.57 (m, 2H), 7.63 (m , 2H), 7.86 (d, 1H), 8.03 (d, 1H), 9.81 (s, 1H)

[준비예 11] IC-11의 합성  Preparation Example 11 Synthesis of IC-11

<단계 1> 6-(5-bromo-2—ni trophenyl )—lH-indole의 합성  <Step 1> Synthesis of 6- (5-bromo-2—ni trophenyl) —lH-indole

Figure imgf000102_0001
Figure imgf000102_0001

Lᅭ brom으 2ᅳ ni trobenzene과 L yo ni trobenzene with brom coming two eu

5-(4,4,5,5-tetramethyl-l,3,2~di oxaboro 1 anᅳ 2ᅳ y 1 )ᅳ 1H_ i ndo 1 e 대신 2,4-dibromo一 1-nitrobenzene과 And 5- (4,4,5,5-tetramethyl-l, 3,2 ~ di oxaboro 1 an eu 2, eu y 1) eu 1H_ i ndo 1 e instead of 2, 4-dibromo一1- nitrobenzene

6-(4，4，5，5— tetramethyl-l,3,2-dioxaborolan-2-yl)— lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 Except for using 6- (4,4,5,5—tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indole, the same procedure as in <Step 2> of Preparation Example 1 was performed.

6- ( 5-bromo-2-n i t r opheny 1 )一 1Hᅳ i ndo 1 e을 얻었다. 6- (5-bromo-2-n i t r opheny 1) 一 1H ᅳ i ndo 1 e was obtained.

¾匪 R: δ 6.51 (d, 1Η), 7.31 (d, 1H) , 7.50 (d, 1H), 7.60 (d, 1H), 7.69 (d, 1H), 7.90 (d, 1H), 8.01 (s, 1H), 8.14 (s, 1H), 8.25 (s, 1H)  ¾ 匪 R: δ 6.51 (d, 1Η), 7.31 (d, 1H), 7.50 (d, 1H), 7.60 (d, 1H), 7.69 (d, 1H), 7.90 (d, 1H), 8.01 (s , 1H), 8.14 (s, 1H), 8.25 (s, 1H)

<단계 2> 6-(5-bromo-2-ni trophenyl )-l-phenyl-lH-indole의 합성  <Step 2> Synthesis of 6- (5-bromo-2-ni trophenyl) -l-phenyl-lH-indole

Figure imgf000102_0002
5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 6ᅳ (5-brotno-2-nitrophenyl)-lH-indole을 사용하는 것을 제외하고는 준비예 1의
Figure imgf000102_0002
Preparation Example 1, except that 6 ᅳ (5-brotno-2-nitrophenyl) -lH-indole obtained in <Step 1> instead of 5- (2-nitr opheny 1)-IH- i ndo 1 e

<단계 3>과 동일한 과정을 수행하여Follow the same process as in <Step 3>

6- ( 5~br omo-2-η i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e-i: 얻었다 . 6- (5 ~ bromo-2-η itr opheny 1)-1-pheny 1-IH-i ndo 1 ei: obtained.

¾ NMR: δ 6.49 (d, IH), 7.30 (d, IH), 7.51 (m, 3H), 7.61 (m, 4H), 7.70 (d, ¾ NMR: δ 6.49 (d, IH), 7.30 (d, IH), 7.51 (m, 3H), 7.61 (m, 4H), 7.70 (d,

IH), 7.91 (d, IH), 8.00 (s, IH), 8:16 (s, IH) IH), 7.91 (d, IH), 8.00 (s, IH), 8:16 (s, IH)

<단계 3> IC-11의 합성  Step 3 Synthesis of IC-11

Figure imgf000103_0001
Figure imgf000103_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 2>에서 얻은 6-(5-bromo-2-nitrophenyl)-l— phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한과정을수행하여 IC-11를 얻었다. Instead of 5- (2-nitr opheny 1)-1-pheny 1-IH- i ndo 1 e, use 6- (5-bromo-2-nitrophenyl) -l— phenyl-lH-indole obtained in <Step 2> Except for that, IC-11 was obtained by performing the same procedure as in <Step 4> of Preparation Example 1.

¾-NMR: δ 6.47 (d, IH) , 7.28 (d, IH)， 7.40 (m, 2H), 7.47 (d, IH), 7.53 (d, IH), 7.59 (m, 3H) , 7.66 (d, IH), 7.87 (d, IH), 8:12 (s, IH), 8.25 (s, IH)  ¾-NMR: δ 6.47 (d, IH), 7.28 (d, IH), 7.40 (m, 2H), 7.47 (d, IH), 7.53 (d, IH), 7.59 (m, 3H), 7.66 (d , IH), 7.87 (d, IH), 8:12 (s, IH), 8.25 (s, IH)

[준비예 12] IC-12의 합성  Preparation Example 12 Synthesis of IC-12

<단계 1> 5-(2-nitrophenyl)-l—으 tolyl-lH-indole의 합성  <Step 1> Synthesis of 5- (2-nitrophenyl) -l—tolyl-lH-indole

Figure imgf000103_0002
Figure imgf000103_0002

nitrobenzene  nitrobenzene

Iodobenzene 대신 l-bromo-2-methylbenzene을 사용하는 것을 제외하고 준비예 1의 <단계 3>과 동일한 과정을 ' 수행하여Except for using l-bromo-2-methylbenzene instead of iodobenzene The same procedure as in <Step 3> of Preparation Example 1, by performing

5-(2-nitrophenyl)-l-o-toly卜 lH-indole을 얻었다.5- (2-nitrophenyl) -l-o-toly 卜 lH-indole was obtained.

-NMR: δ 1.92 (s, 3H), 6.47 (d, 1H), 7.25 (d, 1H) , 7.46 (m, 3H) , 7.56 (m, 3H), 7.64 (t, 1H), 7.85 (t, 1H) , 7.94 (s, 1H) , 8.00 (d, 1H), 8.12 (t, 1H)  -NMR: δ 1.92 (s, 3H), 6.47 (d, 1H), 7.25 (d, 1H), 7.46 (m, 3H), 7.56 (m, 3H), 7.64 (t, 1H), 7.85 (t, 1H), 7.94 (s, 1H), 8.00 (d, 1H), 8.12 (t, 1H)

<단계 2> IC-12의 합성  Step 2 Synthesis of IC-12

Figure imgf000104_0001
Figure imgf000104_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <：단계 1>에서 얻은 5-(2-nitrophenyl)-lᅳ으 tolyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한 과정을 수행하여 IC-12를 얻었다. Except for using 5- (2-nitrophenyl) -l'tolyl-lH-indole obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H-i ndo 1 e Then, the same procedure as in <Step 4> of Preparation Example 1 was carried out to obtain IC-12.

¾-NMR: δ 1.93 (s, 3H), 6.98 (d, 1H), 7.11 (t, 1H), 7.28 (t, 1H), 7.31 (d, 1H), 7.42 (t, 1H), 7.51 (d, 1H), 7.61 (m, 4H), 7.86 (d, 1H), 8.01 (d, 1H), 10.58 (s, 1H)  ¾-NMR: δ 1.93 (s, 3H), 6.98 (d, 1H), 7.11 (t, 1H), 7.28 (t, 1H), 7.31 (d, 1H), 7.42 (t, 1H), 7.51 (d , 1H), 7.61 (m, 4H), 7.86 (d, 1H), 8.01 (d, 1H), 10.58 (s, 1H)

[준비예 13] IC-13의 합성  Preparation Example 13 Synthesis of IC-13

〈단계 j> l—(biphenyl-4-yl)-5-(2-nitrophenyl)-lH-indole의 합성  <Step j> Synthesis of l— (biphenyl-4-yl) -5- (2-nitrophenyl) -lH-indole

Figure imgf000104_0002
Figure imgf000104_0002

lodobenzene 대신 4-bromobi phenyl을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 l-(bi phenyl -4-y l)-5-(2-nitr opheny 1 ) - IH- i ndo 1 e을 얻었다.Preparation Example 1 except that 4-bromobi phenyl instead of lodobenzene The same procedure as in <Step 3> was performed to obtain l- (bi phenyl-4-yl) -5- (2-nitr opheny 1) -IH-i ndo 1 e.

-醒 R: δ 6.73 (d, IH), 7.18 (d, IH), 7.39 (m, 2H), 7.47 (m, 3H), 7.54 (d, IH), 7.59 (m, 3H) , 7.64 (m, 4H), 7.75 (d, 2H), 7.82 (d, IH)  -醒 R: δ 6.73 (d, IH), 7.18 (d, IH), 7.39 (m, 2H), 7.47 (m, 3H), 7.54 (d, IH), 7.59 (m, 3H), 7.64 (m , 4H), 7.75 (d, 2H), 7.82 (d, IH)

<단계 2> IC-13의 합성  <Step 2> Synthesis of IC-13

Figure imgf000105_0001
Figure imgf000105_0001

5-(2-ni trophenyl )-l-phenyl-lH-indole 대신 상기 <단계 1>에서 얻은 l-(bipheny卜 4-yl)-5-(2-nitrophenyl)-lH— indole을 사용하는 것올 제외하고는 준비예 1의 <단계 4>와동일한과정올 수행하여 IC-13를 얻었다.  Except for using l- (bipheny 卜 4-yl) -5- (2-nitrophenyl) -lH— indole obtained in <Step 1> instead of 5- (2-ni trophenyl) -l-phenyl-lH-indole Then, the same procedure as in <Step 4> of Preparation Example 1 was carried out to obtain IC-13.

¾-NMR: δ 6.75 (d, IH), 7.20 (d, IH), 7.42 (m, 2H), 7.51 (m, 3H) , 7.56 (d, IH), 7.62 (m, 3H), 7.68 (m, 3H), 7.76 (d, 2H), 7.85 (d, IH), 10.45 (s, IH)  ¾-NMR: δ 6.75 (d, IH), 7.20 (d, IH), 7.42 (m, 2H), 7.51 (m, 3H), 7.56 (d, IH), 7.62 (m, 3H), 7.68 (m , 3H), 7.76 (d, 2H), 7.85 (d, IH), 10.45 (s, IH)

[준비예 14] IC-14의 합성  Preparation 14 Synthesis of IC-14

<단계 1> IC-14-1의 합성  Step 1 Synthesis of IC-14-1

Figure imgf000105_0002
lodobenzene대신 l—bromo—3,5—di phenyl benzene을사용하는 것올 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 IC-14-1을 얻었다..
Figure imgf000105_0002
Except for using l—bromo—3,5—diphenyl benzene instead of lodobenzene, IC-14-1 was obtained by the same procedure as in <Step 3> of Preparation Example 1.

ᅳ丽 R: δ 6.98 (d, 1H), 7.11 (t, 1H)， 7.24 (t, 1H) , 7.38 (tᅳ 2H) , 7.46 (m, 6H), 7.58 (d, 1H), 7.81 (d, 4H), 7.87 (m, 4H), 7.93 (d, 1H), 7.99 (d, 1H)  ᅳ 丽 R: δ 6.98 (d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (t ᅳ 2H), 7.46 (m, 6H), 7.58 (d, 1H), 7.81 (d , 4H), 7.87 (m, 4H), 7.93 (d, 1H), 7.99 (d, 1H)

<단계 2> IC-14의 합성  Step 2 Synthesis of IC-14

Figure imgf000106_0001
Figure imgf000106_0001

5-(2-ni trophenyl )-l-phenyl-lH- indole 대신 상기 <단계 1>에서 얻은 IC-11-1을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 IC-14를 얻었다.  The same procedure as in <Step 4> of Preparation Example 1 was performed except that IC-11-1 obtained in <Step 1> was used instead of 5- (2-ni trophenyl) -l-phenyl-lH-indole. IC-14 was obtained.

¾-NMR: δ 6.97 (d, 1H), 7.10 (t, 1H), 7.23 (t, 1H), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, 1H), 7.80 (d, 4H), 7.86 (m, 3H), 7.92 (d, 1H), 7.98 (d, 1H)， 10.60 (s, 1H)  ¾-NMR: δ 6.97 (d, 1H), 7.10 (t, 1H), 7.23 (t, 1H), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, 1H), 7.80 (d , 4H), 7.86 (m, 3H), 7.92 (d, 1H), 7.98 (d, 1H), 10.60 (s, 1H)

[준비예 15] IC-15의 합성  Preparation Example 15 Synthesis of IC-15

<단계 1> 5-(2-ni trophenyl )-l-(2-(trifluoromethyOphenyl)-lH— indole의 합성  <Step 1> Synthesis of 5- (2-ni trophenyl) -l- (2- (trifluoromethyOphenyl) -lH—indole

Figure imgf000106_0002
Iodobenzene 대신 1一 bromo一 2一 (tr i fluoromethyl )benzene을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 5-(2-nitrophenyl )-l-(2-(tri f luoromethyl ) phenyl )-lH-indole을 얻었다.
Figure imgf000106_0002
A 5- (2-nitrophenyl) -l- (2- (tri was carried out in the same manner as in <Step 3> of Preparation Example 1, except that 1-l bromo 一 2 一 (tr i fluoromethyl) benzene was used instead of iodobenzene. f luoromethyl) phenyl) -lH-indole was obtained.

¾-NMR: δ 6.48 (d, 1H) , 7.26 (d, 1H) , 7.47 (m, 3H), 7.57 (m, 3H), 7.63 (t, 1H), 7.84 (t, 1H), 7.95 (s, 1H), 8.01 (d, 1H), 8.13 (t, 1H)  ¾-NMR: δ 6.48 (d, 1H), 7.26 (d, 1H), 7.47 (m, 3H), 7.57 (m, 3H), 7.63 (t, 1H), 7.84 (t, 1H), 7.95 (s , 1H), 8.01 (d, 1H), 8.13 (t, 1H)

<단계 2> IC-15의 합성  Step 2 Synthesis of IC-15

Figure imgf000107_0001
Figure imgf000107_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 5-(2-nitrophenyl )-l-(2-(trif luoromethyl ) phenyl )-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한 과정을 수행하여 IC-15를 얻었다.  5- (2-nitrophenyl) -l- (2- (trif luoromethyl) phenyl) -lH obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e Except for using -indole, IC-15 was obtained by following the same procedure as in <Step 4> of Preparation Example 1.

¾-NMR: δ 6.97 (d, 1H), 7.12 (t, 1H), 7.29 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.52 (d, 1H), 7.60 (m, 4H), 7.85 (d, 1H), 8.01 (d, 1H), 10.57 (s, 1H)  ¾-NMR: δ 6.97 (d, 1H), 7.12 (t, 1H), 7.29 (t, 1H), 7.32 (d, 1H), 7.41 (t, 1H), 7.52 (d, 1H), 7.60 (m , 4H), 7.85 (d, 1H), 8.01 (d, 1H), 10.57 (s, 1H)

[준비예 16] IC-16의 합성  Preparation Example 16 Synthesis of IC-16

<단계 1〉 l-(biphenyl-3— yl)-5-(2-nitrophenyl)-lH-indole의 합성  <Step 1> Synthesis of l- (biphenyl-3— yl) -5- (2-nitrophenyl) -lH-indole

Figure imgf000107_0002
Figure imgf000107_0002

Iodobenzene 대신 3-broraobi phenyl을 사용하는 것을 제외하고는 준비예 1의  Preparation Example 1 except that 3-broraobi phenyl instead of iodobenzene

3>과 동일한 과정을 수행하여 l-(bi pheny 1 -3-y 1 ) -5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e을 얻었다.By following the same process as l- (bi pheny 1-3-y 1) -5- (2-nitr opheny 1) -1H-i ndo 1 e was obtained.

-匪 R: δ 6.75 (d, 1H), 7.19 (d, 1H), 7.38 (m, 2H), 7.48 (m, 310， 7.52 (d 1H), 7.58 (m, 3H), 7.65 (m, 4H)， 7.76 (m, 2H) , 7.85 (d, 1H)  -匪 R: δ 6.75 (d, 1H), 7.19 (d, 1H), 7.38 (m, 2H), 7.48 (m, 310, 7.52 (d 1H), 7.58 (m, 3H), 7.65 (m, 4H ), 7.76 (m, 2H), 7.85 (d, 1H)

<단계 2> IC-16의 합성  Step 2 Synthesis of IC-16

Figure imgf000108_0001
Figure imgf000108_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 l-(biphenyl-3-yl)— 5-(2— nitrophenyl)-lH-indole올 사용하는 것을 제외하고는 준비예 1의 <단계 4>와동일한과정을 수행하여 IC-16를 얻었다.  L- (biphenyl-3-yl) — 5- (2—nitrophenyl) -lH-indole obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e Except for using this product, IC-16 was obtained by performing the same procedure as <Step 4> of Preparation Example 1.

¾-醒 R: δ 6.74 (d, 1H), 7.21 (d, 1H), 7.41 (m, 2H), 7.52- (m, 3H), 7.56 (d, 1H), 7.61 (m, 3H), 7.69 (m, 3H), 7.77 (m, 2H), 7.86 (d, 1H), 10.44 (s, 1H)  ¾- 醒 R: δ 6.74 (d, 1H), 7.21 (d, 1H), 7.41 (m, 2H), 7.52- (m, 3H), 7.56 (d, 1H), 7.61 (m, 3H), 7.69 (m, 3H), 7.77 (m, 2H), 7.86 (d, 1H), 10.44 (s, 1H)

[준비예 17] IC-17의 합성  Preparation 17 Synthesis of IC-17

<단계 1> l-(biphenyl-3— yl)— 6-(2-nitrophenyl)-lH-indole의 합성  <Step 1> Synthesis of l- (biphenyl-3—yl) — 6- (2-nitrophenyl) -lH-indole

Figure imgf000108_0002
Figure imgf000108_0002

5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e ^ Iodobenzene 대신 5- (2-n i t r opheny 1)-1H- i ndo 1 e ^ Iodobenzene instead

6-(2-nitrophenyl)-lH-indole과 3-bromobi phenyl를 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여 1- ( b i pheny卜 3-y 1 ) -6- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e을 얻었다.The same procedure as in <Step 3> of Preparation Example 1 was performed except that 6- (2-nitrophenyl) -lH-indole and 3-bromobi phenyl were used. 1- (bi pheny 卜 3-y 1) -6- (2-nitr opheny 1)-1H- i ndo 1 e was obtained.

-薩: δ 6.76 (d, 1H), 7.18 (d, 1H), 7.37 (m, 2H), 7.47 (m, 3H), 7.51 (d 1H), 7.57 (m, 3H), 7.64 (m, 4H), 7.75 (m, 2H), 7.86 (d, 1H)  薩: δ 6.76 (d, 1H), 7.18 (d, 1H), 7.37 (m, 2H), 7.47 (m, 3H), 7.51 (d 1H), 7.57 (m, 3H), 7.64 (m, 4H ), 7.75 (m, 2H), 7.86 (d, 1H)

<단계 2> IC-17의 합성  <Step 2> Synthesis of IC-17

Figure imgf000109_0001
Figure imgf000109_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 l-(biphenyl-3-yl)-6-(2-nitrophenyl)— IH-indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과동일한과정을 수행하여 ICᅳ 17을 얻었다. L- (biphenyl-3-yl) -6- (2-nitrophenyl) —IH-indole obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H-i ndo 1 e Except for using the same procedure as in <Step 4> of Preparation Example 1 to obtain the IC # 17.

-丽 R: δ 6.75 (d, 1H), 7.20 (d, 1H), 7.40 (m, 2H), 7.51 (m, 3H) , 7.57 (d, 1H), 7.62 (m, 3H) , 7.70 (m, 3H), 7.76 (m, 2H), 7.85 (d, 1H) , 10.43 (s, 1H)  -丽 R: δ 6.75 (d, 1H), 7.20 (d, 1H), 7.40 (m, 2H), 7.51 (m, 3H), 7.57 (d, 1H), 7.62 (m, 3H), 7.70 (m , 3H), 7.76 (m, 2H), 7.85 (d, 1H), 10.43 (s, 1H)

[준비예 18] IC-18의 합성  Preparation Example 18 Synthesis of IC-18

〈단계 1> l-(biphenyl-4-yl)-6-(2-nitrophenyl)-lH-indole의 합성  <Step 1> Synthesis of l- (biphenyl-4-yl) -6- (2-nitrophenyl) -lH-indole

Figure imgf000109_0002
Figure imgf000109_0002

5ᅳ ( 2ᅳ n i t r opheny 1 )-lH~i ndo 1 e과 Iodobenzene 대신5 ᅳ (2 ᅳ nitr opheny 1) -lH to i ndo 1 e and Iodobenzene instead

6-(2-nitrophenyl)-lH-indole과 4-bromobi phenyl을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 3>과 동일한 과정을 수행하여The same procedure as in <Step 3> of Preparation Example 1 was performed except that 6- (2-nitrophenyl) -lH-indole and 4-bromobi phenyl were used.

1- ( b i pheny 1 -4-y l)-6-(2-nitr opheny 1 )ᅳ 1H- indo 1 e을 얻었다. ¾-NMR: δ 6.74 (d, 1H), 7.19 (d, 1H), 7.40 (m, 2H), 7.46 (m, 3H), 7.55 (d 1H), 7.58 (m, 3H), 7.63 (m, 4H), 7.75 (d, 2H), 7.83 (d, 1H) 1- (bi pheny 1-4-yl) -6- (2-nitr opheny 1) ᅳ 1H- indo 1 e was obtained. ¾-NMR: δ 6.74 (d, 1H), 7.19 (d, 1H), 7.40 (m, 2H), 7.46 (m, 3H), 7.55 (d 1H), 7.58 (m, 3H), 7.63 (m, 4H), 7.75 (d, 2H), 7.83 (d, 1H)

<단계 2> IC-18의 합성  <Step 2> Synthesis of IC-18

Figure imgf000110_0001
Figure imgf000110_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 l-(biphenyl-4-yl)-6-(2-nitrophenyl)-lH-indole올 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과동일한과정을 수행하여 IC-18을 얻었다.  L- (biphenyl-4-yl) -6- (2-nitrophenyl) -lH-indole obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1 -1H-i ndo 1 e Except for using all the same procedure as in <Step 4> of Preparation Example 1 to obtain the IC-18.

¾-NMR: 5 6.74 (d, 1H), 7.19 (d, 1H), 7.43 (m, 2H), 7.52 (m, 3H), 7.57 (d, 1H), 7.63 (m, 3H), 7.69 (m, 3H), 7.75 (d, 2H), 7.86 (d, 1H), 10.46 (sᅳ 1H)  ¾-NMR: 5 6.74 (d, 1H), 7.19 (d, 1H), 7.43 (m, 2H), 7.52 (m, 3H), 7.57 (d, 1H), 7.63 (m, 3H), 7.69 (m , 3H), 7.75 (d, 2H), 7.86 (d, 1H), 10.46 (s ᅳ 1H)

[준비예 19] IC-19의 합성  Preparation Example 19 Synthesis of IC-19

<단계 1> IC-19-1의 합성  Step 1 Synthesis of IC-19-1

Figure imgf000110_0002
Figure imgf000110_0002

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e^f- Iodobenzene 대신 5- (2-n i t r opheny 1)-1-pheny 1-1H- i ndo 1 e ^ f- Iodobenzene instead

6-(2-nitr opheny 1 ) - 1H- i ndo 1 e3} 1-br omo-3 , 5~d i pheny 1 benzene을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과동일한과정을수행하여 IC-19-1을 얻었다. 6- (2-nitr opheny 1)-1H- i ndo 1 e 3 } Follow the same procedure as in <Step 3> of Preparation Example 1, except that 1-br omo-3 and 5 to di pheny 1 benzene are used. Was carried out to obtain IC-19-1.

¾-NMR: δ 6.98 (d, 1H), 7.11 (t, 1H)， 7.24 (t, 1H)， 7.38 (m, 2H), 7.45 (m, 6H), 7.57 (d, IH), 7.80 (d, 4H), 7.86 (m, 4H), 7.92 (d, IH), 7.98 (d, IH)¾-NMR: δ 6.98 (d, 1H), 7.11 (t, 1H), 7.24 (t, 1H), 7.38 (m, 2H), 7.45 (m, 6H), 7.57 (d, IH), 7.80 (d, 4H), 7.86 (m, 4H), 7.92 (d, IH), 7.98 (d, IH)

<단계 2> IC-19의 합성 Step 2 Synthesis of IC-19

Figure imgf000111_0001
Figure imgf000111_0001

5- ( 2-n i t r opheny 1 ) -1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 IC— 19-1을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-19를 얻었다. <Step 4> of Preparation Example 1, except that IC 19-1 obtained in <Step 1> was used instead of 5- (2-nitr opheny 1) -1-pheny 1 -IH-i ndo 1 e. IC-19 was obtained by performing the same procedure as in the following.

-丽： δ 6.97 (d, IH), 7.10 (t, IH), 7.23 (t, IH)， 7.37 (t, 2H) , 7.45 (m, 6H), 7.58 (d, IH), 7.80 (d, 4H), 7.86 (m, 3H), 7.92 (d, IH), 7.98 (d, IH), 10.59 (s, IH)  -Δ 6.97 (d, IH), 7.10 (t, IH), 7.23 (t, IH), 7.37 (t, 2H), 7.45 (m, 6H), 7.58 (d, IH), 7.80 (d, 4H), 7.86 (m, 3H), 7.92 (d, IH), 7.98 (d, IH), 10.59 (s, IH)

[준비예 20] IC-20의 합성  Preparation Example 20 Synthesis of IC-20

<단계 1> 6-(2-nitrophenyl )-1-(3-( tr if luoromethyl )phenyl )-lH-indole의  <Step 1> of 6- (2-nitrophenyl) -1- (3- (tr if luoromethyl) phenyl) -lH-indole

Figure imgf000111_0002
Figure imgf000111_0002

nitrobenzene  nitrobenzene

5-(2ᅳ ni trophenyl )ᅳ 1ᅳ phenylᅳ lH_indole과 Iodobenzene 대신 6一 (2— nitrophenyl )— IH一 indole과 1一 bromo一 3— (tr i uoromethyl )benzene을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 6-(2-ni trophenyl)-l-(3-(tr i f luoromethyl ) phenyl )—1Η_ indole을 얻었다 .Preparation example except for the use of 6 一 (2—nitrophenyl) — IH in indole and 1 bro bromo 3 3— (tr i uoromethyl) benzene instead of 5- (2 ᅳ ni trophenyl) ᅳ 1 ᅳ phenyl ᅳ lH_indole and Iodobenzene Follow the same process as in <Step 3> of 1 6- (2-ni trophenyl) -l- (3- (tr if luoromethyl) phenyl) —1Η_ indole was obtained.

¾-NMR: δ 6.80 (d, 1H), 7.11 (t, 1H), 7.21 (t, 1H) , 7.36 (s, 1H), 7.42 (s 1H), 7.50 (m, 2H), 7.55 (ra, 2H), 7.63 (m, 2H), 7.86 (d, 1H), 8.01 (d, 1H) ¾-NMR: δ 6.80 (d, 1H), 7.11 (t, 1H), 7.21 (t, 1H), 7.36 (s, 1H), 7.42 (s 1H), 7.50 (m, 2H), 7.55 (ra, 2H), 7.63 (m, 2H), 7.86 (d, 1H), 8.01 (d, 1H)

<단계 2> IC-20의 합성  Step 2 Synthesis of IC-20

Figure imgf000112_0001
Figure imgf000112_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 6-(2-nitrophenyl)— l-(3-(trinuoromethyl)phenyl)-lH-indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-20을 얻었다.  6- (2-nitrophenyl) — l- (3- (trinuoromethyl) phenyl) -lH- obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e Except for using indole was carried out the same process as in <Step 4> of Preparation Example 1 to obtain an IC-20.

¾-NMR: δ 6.81 (d, 1H), 7.12 (t, 1H)， 7.24 (t, 1H) , 7.43 (d, 1H) , 7.51 (m, 2H), 7.58 On, 2H), 7.64 (m, 2H), 7.85 (d, 1H), 8.02 (d, 1H), 9.82 (s, 1H)  ¾-NMR: δ 6.81 (d, 1H), 7.12 (t, 1H), 7.24 (t, 1H), 7.43 (d, 1H), 7.51 (m, 2H), 7.58 On, 2H), 7.64 (m, 2H), 7.85 (d, 1H), 8.02 (d, 1H), 9.82 (s, 1H)

[준비예 21] IC-21와합성  Preparation Example 21 Synthesis with IC-21

<단계 1> 3— (5-(2-nitrophenyl)-lH-indol-l-yl)-9-phenyl-9H-carbazole의 합성  <Step 1> 3— Synthesis of (5- (2-nitrophenyl) -lH-indol-l-yl) -9-phenyl-9H-carbazole

Figure imgf000112_0002
Figure imgf000112_0002

5- (2-ni tropheny 1 )-lH-indole^f Iodobenzene 대신 5- (2-ni tropheny 1) -lH-indole ^ f instead of iodobenzene

6-(2-nitrophenyl)-lH-indole과 3-bronK)-9-phenyl-9H-carbazole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 3-(5-(2-nitr opheny 1 ) - IH- i ndo 1ᅳ 1-y 1 ) -9-pheny l-9H_carbazole을 얻었다. The use of 6- (2-nitrophenyl) -lH-indole and 3-bronK) -9-phenyl-9H-carbazole Except for <Step 3> of Preparation Example 1, except that 3- (5- (2-nitr opheny 1) -IH-i ndo 1 n 1-y 1) -9-pheny l-9H_carbazole was obtained. .

GC-Mass (이론치: 479.16 g/mol, 측정치: 479 g/mol)  GC-Mass (Theoretical value: 479.16 g / mol, Measured value: 479 g / mol)

<단계 2> IC-21의 합성  <Step 2> Synthesis of IC-21

Figure imgf000113_0001
Figure imgf000113_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 3-(5-( 2-n i tr opheny l)-lH-indol- 1-y 1 ) -9-pheny 1 -9H-carbazo 1 e을 사용하는 것을 제외하고는상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-21을 얻었다.  3- (5- (2-ni tr opheny l) -lH-indol-1-y obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-IH- i ndo 1 e 1) Except for using -9-pheny 1 -9H-carbazo 1 e was carried out the same procedure as in <step 4> of Preparation Example 1 to obtain an IC-21.

GC-Mass (이론치: 447.17 g/mol, 측정치: 447 g/mol)  GC-Mass (Theoretical value: 447.17 g / mol, Measured value: 447 g / mol)

[준비예 22] IC-22의 합성 Preparation Example 22 Synthesis of IC-22

Figure imgf000113_0002
Figure imgf000113_0002

9-(4,6-di heny 1 - 1 , 3 , 5- 1 r i az i η-2-y 1 ) -3- ( 5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 - 1-y 1 ) -9H~c a rbazole의 합성 9- (4,6-di heny 1-1, 3, 5- 1 ri az i η- 2-y 1) -3- (5- (2-nitr opheny 1)-IH- i ndo 1-1- y 1) -9H ~ synthesis of ca rbazole

Figure imgf000113_0003
5ᅳ (2一 nitrophenyl)ᅳ 1Hᅳ indole과 Iodobenzene 대신
Figure imgf000113_0003
5 ᅳ (2 一 nitrophenyl) ᅳ instead of 1H ᅳ indole and Iodobenzene

6-(2-ni trophenyl )~1Hᅳ indole괴" 6- (2-ni trophenyl) to 1H ᅳ indole ingot "

3-brom으 9ᅳ (4， 6-d i pheny 1-1,3,5-tr iazi η-2-yl )-9H-carbazo 1 e을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 9- (4, 6-d i heny 1 - 1 , 3， 5— t r i az i n— 2— y 1 )—3— ( 5— ( 2—n i t r opheny 1 )-lH-indol-l-yl )-9H-ca rbazole올 얻었다.  <Step 3> of Preparation Example 1, except 9- (4, 6-dipheny 1-1,3,5-tr iazi η-2-yl) -9H-carbazo 1 e as 3-brom was used. 9- (4, 6-di heny 1-1, 3 ， 5— tri az in— 2— y 1) —3— (5— (2—nitr opheny 1) -lH-indol- l-yl) -9H-ca rbazole was obtained.

GC-Mass (이론치 : 634.21 g/mol, 측정치 : 634 g/mol)  GC-Mass (Theoretical value: 634.21 g / mol, Measured value: 634 g / mol)

<단계 2> IC-22의 합성  <Step 2> Synthesis of IC-22

Figure imgf000114_0001
Figure imgf000114_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 5- (2-n i t r opheny 1)-1-pheny 1-1H- i ndo 1 e obtained in <Step 1> instead of

9- ( 4 , 6-d i pheny 1 - 1 , 3 , 5- 1 r i az i η-2-y 1 ) -3- ( 5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 - 1-y 1 ) -9H-ca rbazole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-22올 얻었다. 9- (4, 6-di pheny 1-1, 3, 5- 1 ri az i η-2-y 1) -3- (5- (2-nitr opheny 1)-1H- i ndo 1-1- y 1) except for using -9H-ca rbazole was carried out the same process as in <Step 4> of Preparation Example 1 to obtain IC-22ol.

GC-Mass (이론치: 602.22 g/mol, 측정치: 602 g/mol)  GC-Mass (Theoretical value: 602.22 g / mol, Measured value: 602 g / mol)

[준비예 23] IC-23의 합성  Preparation Example 23 Synthesis of IC-23

<단계 1> 5-bromo-2-phenyl-lH-indole의 합성

Figure imgf000115_0001
<Step 1> Synthesis of 5-bromo-2-phenyl-lH-indole
Figure imgf000115_0001

질소 기류 하에서 5-bromo-lH- indole (25 g, 0.13 mol), Iodobenzene (31.22 g, 0.15 mol), Pd(0Ac)2 (1.43'g, 5 raol%), Triphenylphosphine (1.67 g, 5 mol%), KOAc (37.55 g, 0.38 mol)및 ¾0 (300 ml)를혼합하고 110°C에서 24시간 동안 교반하였다. 반응이 종결된 후 에틸아세테이트로 추출한 다음 MgS04로 수분을 제거하고， 컬럼크로마토그래피 (Hexane:EA = 10： 1 (v/v))로 정제하여5-bromo-lH-indole (25 g, 0.13 mol), Iodobenzene (31.22 g, 0.15 mol), Pd (0Ac) 2 (1.43 ' g, 5 raol%), Triphenylphosphine (1.67 g, 5 mol%) under nitrogen stream ), KOAc (37.55 g, 0.38 mol) and ¾0 (300 ml) were mixed and stirred at 110 ° C for 24 h. After the reaction was completed, the mixture was extracted with ethyl acetate, followed by removing moisture with MgS0 4 , and purified by column chromatography (Hexane: EA = 10: 1 (v / v)).

5-br omo-2-pheny 1 - 1H- i ndo 1 e (16.66 g, 수율 48%)을 얻었다. 5-br omo-2-pheny 1 -1H-i ndo 1 e (16.66 g, yield 48%) was obtained.

^-NMR: δ 6.89 (dd, 1H), 7.20 (dd, 1H) , 7.34 (m, 1H), 7.36 (d, 1H), 7.47 (t, 2H), 7.71 (d, 1H), 7.86 (dd, 2H), 11.74 (s, 1H)  ^ -NMR: δ 6.89 (dd, 1H), 7.20 (dd, 1H), 7.34 (m, 1H), 7.36 (d, 1H), 7.47 (t, 2H), 7.71 (d, 1H), 7.86 (dd , 2H), 11.74 (s, 1H)

<단계 2 5-(2-n rophenyl)-2-phenyl-lH-indole의 합성  <Step 2 Synthesis of 5- (2-n rophenyl) -2-phenyl-lH-indole

Figure imgf000115_0002
Figure imgf000115_0002

질소 기류 하에서 2-nitrophenylboronic acid (11.04 g, 66.14 mmol)과 상기 <단계 1>에서 얻은 5-br orao-2-pheny 1 - 1H- i ndo 1 e (15 g, 55.12瞧 ol), NaOH (6.61 g, 165.36 mmol) 및 THFVH20(200 ml八 00 ml)를 흔합한다음， 40°C에서 Pd(PPh3)4(3.18 g, 5 mol)를 넣고 80°C에서 12시간동안교반하였다. 2-nitrophenylboronic acid (11.04 g, 66.14 mmol) under nitrogen stream and 5-br orao-2-pheny 1 -1H-i ndo 1 e (15 g, 55.12. Ol) obtained in <Step 1>, NaOH (6.61 g, 165.36 mmol) and THFVH 2 0 (200 ml八00 ml) to Pd (PPh 3) in a combined common and then, 40 ° C 4 (3.18 g , into a 5 mol) was stirred at 80 ° C for 12 hours.

반응 종결 후 메틸렌클로라이드로추출하고 MgS04를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:EA = 5:1 (v/v))로 정제하여 5- ( 2-η ί t r opheny 1 ) -2-pheny 1 - 1H- i ndo 1 e (10.74 g, 수율 62%)을 얻었다. -丽： δ 6.88 (dd, 1Η), 7.21 (d, 1H), 7.32 (m, 1H), 7.34 (d, 1H), 7.46 (m, 3H), 7.64 (m, 2H), 7.77 (d, 2H), 8.02 (d, 2H), 11.73 (s, 1H) After completion of the reaction, the mixture was extracted with methylene chloride and MgS0 4 was added and filtered. The solvent was removed from the obtained organic layer and purified by column chromatography (Hexane: EA = 5: 1 (v / v)) to give 5- (2-η ί tr opheny 1) -2-pheny 1-1H- i ndo 1 e (10.74 g, yield 62%) was obtained. -丽 ： δ 6.88 (dd, 1Η), 7.21 (d, 1H), 7.32 (m, 1H), 7.34 (d, 1H), 7.46 (m, 3H), 7.64 (m, 2H), 7.77 (d, 2H), 8.02 (d, 2H), 11.73 (s, 1H)

<단계 3> 5-(2ᅳ 0^60¥1)-1,2-^1± 1^-111-^(1016의 합성  <Step 3> 5- (2 ᅳ 0 ^ 60 ¥ 1) -1,2- ^ 1 ± 1 ^ -111-^ (synthesis of 1016

Figure imgf000116_0001
Figure imgf000116_0001

5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e 대신 상기 <단계 2>에서 얻은 5-(2-nitrophenyl)-2-phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 5-(2-nitrophenyl)-l,2-diphenyl-lH-indole을 얻었다.  Preparation Example 1 except for using 5- (2-nitrophenyl) -2-phenyl-lH-indole obtained in <Step 2> instead of 5- (2-nitr opheny 1)-1H- i ndo 1 e The same procedure as in <Step 3> was performed to obtain 5- (2-nitrophenyl) -l, 2-diphenyl-lH-indole.

GC-Mass (이론치: 390.14 g/mol, 측정치: 390 g/mol)  GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

<단계 3> IC-23의 합성  <Step 3> Synthesis of IC-23

Figure imgf000116_0002
Figure imgf000116_0002

5- ( 2-n i t r opheny 1 ) -1-pheny 1 -1H- i ndo 1 e 대신 상기 <단계 3>에서 얻은 5- (2-n it rophenyl)-l, 2-di phenyl -1H- indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한과정을수행하여 IC-23을 얻었다.  Instead of 5- (2-nitr opheny 1) -1-pheny 1 -1H-i ndo 1 e, 5- (2-n it rophenyl) -l and 2-di phenyl -1H-indole obtained in <Step 3> Except for using the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-23.

GC-Mass (이론치: 358.15 g/mol, 측정치: 358 g/mol)  GC-Mass (Theoretical value: 358.15 g / mol, Measured value: 358 g / mol)

[준비예 24] IC-24의 합성  Preparation Example 24 Synthesis of IC-24

<단계 1> 6-chloro-2-phenyl-lH-indole의 합성

Figure imgf000117_0001
<Step 1> Synthesis of 6-chloro-2-phenyl-lH-indole
Figure imgf000117_0001

5ᅳ bromo_lHᅳ indole과 Iodobenzene 대신 6ᅳ chkir으 1Hᅳ indole과 bromobenzene올 사용하는 것을 제외하고는 상기 준비예 23의 <단계 1>과 동일한 과정을수행하여 6-chloro-2-phenyl-lHᅳ indole을 얻었다.  Except for using 5 ᅳ bromo_lH ᅳ indole and Iodobenzene instead of 6 ᅳ chkir, 1H ᅳ indole and bromobenzeneol were carried out in the same manner as in <Step 1> of Preparation Example 23, followed by 6-chloro-2-phenyl-lH ᅳ indole Got.

¾-NMR: δ 6.92 (d, 1H), 7.02 (dd, 1H) , 7.33 (t, 1H) , 7.41 (s, 1H), 7.47 ¾-NMR: δ 6.92 (d, 1H), 7.02 (dd, 1H), 7.33 (t, 1H), 7.41 (s, 1H), 7.47

(t, 2H), 7.54 (d, 1H), 7.85 (d, 2H), 11.68 (s, 1H) (t, 2H), 7.54 (d, 1H), 7.85 (d, 2H), 11.68 (s, 1H)

<단계 2> 6-(2-nitrophenyl)— 2— phenyl-lH-indole의 합성  <Step 2> Synthesis of 6- (2-nitrophenyl) — 2— phenyl-lH-indole

Figure imgf000117_0002
Figure imgf000117_0002

5-br omo-2-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 6-chloro-2-phenyl-lH-indole을 사용하는 것을 제외하고는 상기 준비예 23의 <단계 2>와동일한 과정을 수행하여 6- (2-n it rophenyl)ᅳ 2-phenyl -1H- indole을 얻었다.  <Step 2 of Preparation Example 23, except that 6-chloro-2-phenyl-lH-indole obtained in <Step 1> was used instead of 5-br omo-2-pheny 1 -1H-i ndo 1 e > The same process as to obtain 6- (2-n it rophenyl) ᅳ 2-phenyl -1H- indole.

ᅳ NMR: δ 6.91 (d, 1H), 7.03 (d, 1H) , 7.31 (t, 1H) , 7.42 (s, 1H) , 7.48 (m, H), 7.53 (d, 1H), 7.76 (m, 3H), 8.01 (d, 2H), 11.66 (s, 1H)  MR NMR: δ 6.91 (d, 1H), 7.03 (d, 1H), 7.31 (t, 1H), 7.42 (s, 1H), 7.48 (m, H), 7.53 (d, 1H), 7.76 (m, 3H), 8.01 (d, 2H), 11.66 (s, 1H)

<단계 3> 6-(2-nitrophenyl)-l,2-diphenyl-lH-indole의 합성  Step 3 Synthesis of 6- (2-nitrophenyl) -l, 2-diphenyl-lH-indole

Figure imgf000117_0003
Figure imgf000117_0003

5- ( 2-n i t r opheny 1 ) - 1H- i ndo 1 e 대신 상기 <단계 2>에서 얻은 6-(2-nitrophenyl)-2-phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 6-(2-nitrophenyl)-l,2-diphenyl-lH-indole을 얻었다. 5- (2-nitr opheny 1)-1H- i ndo 1 e obtained in <Step 2> instead of Except for using 6- (2-nitrophenyl) -2-phenyl-lH-indole, 6- (2-nitrophenyl) -l, 2-diphenyl- lH-indole was obtained.

GC-Mass (이론치 : 390.14 g/mol, 측정치: 390 g/mol)  GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

<단계 4> IC-24의 합성  Step 4 Synthesis of IC-24

Figure imgf000118_0001
Figure imgf000118_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 2>에서 얻은 6-(2-nitrophenyl)— l,2-diphenyl-lH-indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-24를 얻었다.  Use of 6- (2-nitrophenyl) — l, 2-diphenyl-lH-indole obtained in <Step 2> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e Except for the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-24.

GC-Mass (이론치: 358.15 g/mol, 측정치: 358 g/mol)  GC-Mass (Theoretical value: 358.15 g / mol, Measured value: 358 g / mol)

[준비예 25] IC-25의 합성  Preparation Example 25 Synthesis of IC-25

<단계 1> 6— chloro-3-phenyl-lH-indole의 합성  <Step 1> 6— Synthesis of chloro-3-phenyl-lH-indole

Figure imgf000118_0002
Figure imgf000118_0002

질소 기류 하에서 6-ch lor으 LH- indole (25 g, 0.17 mol), bromobenzene (31.19 g, 0.20 mol), Pd(0Ac)2 (1.86 g, 5 mol), Triphenylphosphine (2.17 g, 5 mol%), 2C03 (68.64 g, 0.50 mol) 및 1,4-dioxane (300 ml)를 흔합하고 130°C에서 18시간 동안 교반하였다. L-indole (25 g, 0.17 mol), bromobenzene (31.19 g, 0.20 mol), Pd (0Ac) 2 (1.86 g, 5 mol), Triphenylphosphine (2.17 g, 5 mol%) in 6-ch lor under nitrogen stream , 2 CO 3 (68.64 g, 0.50 mol) and 1,4-dioxane (300 ml) were combined and stirred at 130 ° C. for 18 hours.

반응이 종결된 후 에틸아세테이트로 추출한 다음 MgS04로 수분을 제거하고， 컬럼크로마토그래피 (Hexane:EA = 10： 1 (v/v))로 정제하여After the reaction was completed, the mixture was extracted with ethyl acetate and then water was removed with MgS0 4 . Purified by column chromatography (Hexane: EA = 10: 1 (v / v))

6-ch 1 or ο-3-pheny 1 - IH- i ndo 1 e (24.5 gᅳ수율 65%)을 얻었다.6-ch 1 or ο-3-pheny 1-IH- i ndo 1 e (24.5 g 율 yield 65%) was obtained.

-丽 R: δ 7.10 (dd, IH), 7.25 (m, IH), 7.43 (t, 2H), 7.49 (d, IH), 7.67 (dd, 2H), 7.73 (d, IH), 7.85 (d, IH), 11.49 (s, IH)  -R: δ 7.10 (dd, IH), 7.25 (m, IH), 7.43 (t, 2H), 7.49 (d, IH), 7.67 (dd, 2H), 7.73 (d, IH), 7.85 (d , IH), 11.49 (s, IH)

<단계 2> 6-(2-nitrophenyl)-3-phenyl-lH-indole의 합성  <Step 2> Synthesis of 6- (2-nitrophenyl) -3-phenyl-lH-indole

Figure imgf000119_0001
Figure imgf000119_0001

5-br omo-2-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 6-chlon)-3-phenyl-lH-indole을 사용하는 것을 제외하고는 상기 준비예 23의 <단계 2>와동일한 과정을 수행하여 6-(2ᅳ nitrophenyl )-3-phenyl-lH-indole을 얻었다.  <Step 1 of Preparation Example 23 except that 6-chlon) -3-phenyl-lH-indole obtained in <Step 1> was used instead of 5-br omo-2-pheny 1 -IH-i ndo 1 e. 2> was carried out the same process as 6- (2 ᅳ nitrophenyl) -3-phenyl-lH-indole.

ᅳ NMR: δ 7.11 (d, IH), 7.26 (m, IH) , 7.44 (t, 2H), 7.48 (m, 2H), 7.55 (m, 3H), 7.61 (d, IH), 7.73 (d, IH), 8.00 (d, 2H), 11.48 (s, IH)  MR NMR: δ 7.11 (d, IH), 7.26 (m, IH), 7.44 (t, 2H), 7.48 (m, 2H), 7.55 (m, 3H), 7.61 (d, IH), 7.73 (d, IH), 8.00 (d, 2H), 11.48 (s, IH)

<단계 3> 6— (2-nitrophenyl)-l,3-diphenyl-lH-indole의 합성  Step 3 Synthesis of 6— (2-nitrophenyl) -l, 3-diphenyl-lH-indole

Figure imgf000119_0002
Figure imgf000119_0002

5- ( 2-ni tr opheny 1 )-lH-indole 대신 상기 <단계 2>에서 얻은 6-(2-nitrophenyl)-3-phenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 6ᅳ (2-nitrophenyl)-l,3-diphenyl-lH-indole을 얻었다. GC-Mass (이론치: 390.14 g/mol, 측정치: 390 g/mol) <Step of Preparation Example 1 except that 6- (2-nitrophenyl) -3-phenyl-lH-indole obtained in <Step 2> was used instead of 5- (2-ni tr opheny 1) -lH-indole. The procedure of 3> was followed to obtain 6 ᅳ (2-nitrophenyl) -l, 3-diphenyl-lH-indole. GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

<단계 4> IC-25의 합성  Step 4 Synthesis of IC-25

Figure imgf000120_0001
Figure imgf000120_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 3>에서  5- (2-n i t r opheny 1)-1-pheny 1-1H- i ndo 1 e instead of <Step 3>

6-(2-nitrophenyl)-l,3ᅳ dipheny卜 lH-indole을 사용하는 것을 제외하고는

Figure imgf000120_0002
준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-25을 얻었다. Except for using 6- (2-nitrophenyl) -l, 3, dipheny 卜 lH-indole
Figure imgf000120_0002
IC-25 was obtained in the same manner as in <Step 4> of Preparation Example 1.

GC-Mass (이론치: 358.15 g/mol, 측정치: 358 g/mol)  GC-Mass (Theoretical value: 358.15 g / mol, Measured value: 358 g / mol)

[준비예 26] IC-26의 합성  Preparation 26 Synthesis of IC-26

<단계 1> 5-br omo-2, 3-d i phenyl -1H- indole의 합성  <Step 1> Synthesis of 5-br omo-2, 3-d i phenyl -1H- indole

Figure imgf000120_0003
Figure imgf000120_0003

6-chloro-lH- indole 대신 5-brotno-2-phenyl-lH-indole을 사용하는 것을 제외하고는 상기 준비예 25의 <단계 1>과 동일한 과정을 수행하여 5-brorao-2， 3-d i pheny卜 1H- i ndo 1 e올 얻었다. Except for using 5-brotno-2-phenyl-lH-indole instead of 6-chloro-lH- indole was carried out the same process as in <Step 1> of Preparation Example 25 to 5-brorao-2 ， 3-di pheny 卜 1H-i ndo 1 eol was obtained.

-画 R: δ 7.23 (d, 1H), 7.31 (t, 2H), 7.43 (m, 6H), 7.67 (d, 1H), 7.71 (d, 1H), 7.84 (d, 2H), 11.34 (s, 1H)  -画 R: δ 7.23 (d, 1H), 7.31 (t, 2H), 7.43 (m, 6H), 7.67 (d, 1H), 7.71 (d, 1H), 7.84 (d, 2H), 11.34 (s , 1H)

<：단계 2> 5-(2-nitrophenyl)-2,3-diphenyl-lH-indole의 합성 < ： Step 2> Synthesis of 5- (2-nitrophenyl) -2,3-diphenyl-lH-indole

Figure imgf000121_0001
Figure imgf000121_0001

5-br omo-2-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 5-bromo-2,3-diphenyl-lH-indole을 사용하는 것을 제외하고는 상기 준비예 23의 <단계 2>와 동일한 과정을 수행하여 5-(2-nitrophenyO-2,3-diphenyl-lH-indole을 얻었다.  Except for using 5-bromo-2,3-diphenyl-lH-indole obtained in <Step 1> instead of 5-br omo-2-pheny 1 -IH-i ndo 1 e < The procedure of step 2> was followed to obtain 5- (2-nitrophenyO-2,3-diphenyl-lH-indole.

GC-Mass (이론치: 390.14 g/mol, 측정치: 390 g/mol)  GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

<단계 3> 5-(2-nitrophenyl)-2,3— diphenyl-lH-indole의 합성  <Step 3> Synthesis of 5- (2-nitrophenyl) -2,3—diphenyl-lH-indole

Figure imgf000121_0002
Figure imgf000121_0002

5- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 상기 <단계 2>에서 얻은 5-(2-nitrophenyl)-2,3-diphenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 과정을 수행하여 Preparation Example except that 5- (2-nitrophenyl) -2,3-diphenyl-lH-indole obtained in <Step 2> was used instead of 5- (2-nitr opheny 1) -IH-i ndo 1 e Follow the same process as in <Step 3> of 1

5- On i t ropheny 1 ) - 1ᅳ 2 , 3- 1 r i pheny 1ᅳ IH- i ndo 1 e을 얻었다. 5- On i t ropheny 1)-1 ᅳ 2, 3- 1 r i pheny 1 ᅳ IH- i ndo 1 e were obtained.

GC-Mass (이론치: 466.17 g/mol, 측정치: 466 g/mol)  GC-Mass (Theoretical value: 466.17 g / mol, Measured value: 466 g / mol)

<단계 4> IC-26의 합성  Step 4 Synthesis of IC-26

Figure imgf000121_0003
5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 3>에서 얻은 5-(2-nitrophenyl)-l,2,3— triphenyl-ΙΗ— indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과동일한 과정을수행하여 IC-23을 얻었다.
Figure imgf000121_0003
Instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e, use 5- (2-nitrophenyl) -l, 2,3—triphenyl-ΙΗ— indole obtained in <Step 3> above Except for, the same procedure as in <Step 4> of Preparation Example 1 was carried out to obtain IC-23.

GC-Mass (이론치: 434.18 g/mol, 측정치: 434 g/mol)  GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

[준비예 27] IC-27의 합성  Preparation 27 Synthesis of IC-27

<단계 1> 6-ch 1οπ3-2, 3-d i phenyl -1H- indole의 합성  <Step 1> Synthesis of 6-ch 1οπ3-2, 3-d i phenyl -1H-indole

Figure imgf000122_0001
Figure imgf000122_0001

6-chloro-lH-indole 대신 6-chlon)-2-phenyl-lH-indole올 사용하는 것을 제외하고는 상기 준비예 25의 <단계 1>과 동일한 과정을 수행하여 6-ch 1 or 0-2， 3-d i pheny 1 -1H— i ndo 1 e을 얻었다.  Except for using 6-chlon) -2-phenyl-lH-indoleol instead of 6-chloro-lH-indole to perform the same process as in <Step 1> of Preparation Example 25 6-ch 1 or 0-2 , 3-di pheny 1 -1H— i ndo 1 e was obtained.

¾-NMR: δ 7.18 (d, 1H), 7.29 (t, 2H), 7.50 (m, 6H)ᅳ 7.62 (d, 1H), 7.75 (d, 1H), 7.89 (dᅳ 2H), 11.35 (s, 1H)  ¾-NMR: δ 7.18 (d, 1H), 7.29 (t, 2H), 7.50 (m, 6H) ᅳ 7.62 (d, 1H), 7.75 (d, 1H), 7.89 (d ᅳ 2H), 11.35 (s , 1H)

<단계 2> 6-(2-nitrophenyl)-2,3-diphenyl-lH-indole의 합성  Step 2 Synthesis of 6- (2-nitrophenyl) -2,3-diphenyl-lH-indole

Figure imgf000122_0002
Figure imgf000122_0002

5-br omo-2-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 6-ch 1οπ)-2, 3-d i pheny 1-lH- indole을 사용하는 것을 제외하고는 상기 준비예 23의 <단계 2>와 동일한 과정을 수행하여 6ᅳ (2-nitrophenyl)-2,3-diphenyl-lH-indole을 얻었다. GC-Mass (이론치 : 390.14 g/mol, 측정치: 390 g/mol) The preparation above except using 6-ch 1οπ) -2 and 3-di pheny 1-lH-indole obtained in <Step 1> instead of 5-br omo-2-pheny 1-1H-i ndo 1 e The same procedure as in <Step 2> of Example 23 was performed to obtain 6 ′ (2-nitrophenyl) -2,3-diphenyl-lH-indole. GC-Mass (Theoretical value: 390.14 g / mol, Measured value: 390 g / mol)

<단계 3> 6-(2-nitrophenyl)-l,2,3-triphenyl-lH-indole의 합성  Step 3 Synthesis of 6- (2-nitrophenyl) -l, 2,3-triphenyl-lH-indole

Figure imgf000123_0001
Figure imgf000123_0001

5- ( 2-n i t r opheny 1 ) -IH- i ndo 1 e 대신 상기 <단계 2>에서 얻은 6-(2-nitrophenyl)-2,3-diphenyl-lH-indole을 사용하는 것을 제외하고는 준비예 1의 <단계 3>과 동일한 정을 수행하여 Preparation Example except using 6- (2-nitrophenyl) -2,3-diphenyl-lH-indole obtained in <Step 2> instead of 5- (2-nitr opheny 1) -IH-i ndo 1 e Follow the same definition as in <Step 3> of 1

6- ( 2-n i t r opheny 1 ) - 1， 2， 3— t r i pheny 1 - IH- i ndo 1 e을 얻었다. 6- (2-n i t r opheny 1)-1, 2, 3— t r i pheny 1-IH- i ndo 1 e was obtained.

GC-Mass (이론치: 466.17 g/mol, 측정치: 466 g/mol)  GC-Mass (Theoretical value: 466.17 g / mol, Measured value: 466 g / mol)

<단계 4> IC-27의 합성  Step 4 Synthesis of IC-27

Figure imgf000123_0002
Figure imgf000123_0002

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 -IH- i ndo 1 e 대신 상기 <단계 3>에서 얻은 6-(2-nitrophenyl)-l,2,3-triphenyl— lH-indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을수행하여 IC-27을 얻었다.  Instead of 5- (2-nitr opheny 1)-1-pheny 1 -IH- i ndo 1 e, use 6- (2-nitrophenyl) -l, 2,3-triphenyl— lH-indole obtained in <Step 3> Except for, the same procedure as in <Step 4> of Preparation Example 1 was carried out to obtain IC-27.

GC-Mass (이론치: 434.18 g/mol, 측정치: 434 g/mol)  GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

[준비예 28] IC-28의 합성 Preparation Example 28 Synthesis of IC-28

Figure imgf000123_0003
Figure imgf000123_0003

1-(3-(4, 6一 d i pheny 1-1,3,5-triazi η-2-y 1 ) pheny l)~6-(2-nitr opheny 1 ) - IH- i ndo 1 e의 // z-sosZSSMld 6 OAV 1- (3- (4, 6 一 di pheny 1-1,3,5-triazi η-2-y 1) pheny l) to 6- (2-nitr opheny 1)-of IH- i ndo 1 e // z-sos Z SSM ld 6 OA V

Figure imgf000124_0001
Figure imgf000124_0001

^)s ΐ j Τ2q j μ g fᅳqg ΛpΗl 1g p 911ΐ；Tsd :do U§d3 ou Alsl -- -I - - - 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-28올 얻었다. ^ ) s ΐ j Τ2q j μ gf ᅳ qg ΛpΗ l 1 gp 9 11ΐ ; Tsd : do U§d3 ou A l s l --I--- Except for using the same procedure as in <Step 4> of Preparation Example 1 to obtain an IC-28ol.

GC-Mass (이론치: 513.20 g/mol, 측정치: 513 g/raol)  GC-Mass (Theoretical value: 513.20 g / mol, Measured value: 513 g / raol)

[준비예 29] IC-29의 합성 Preparation Example 29 Synthesis of IC-29

Figure imgf000125_0001
Figure imgf000125_0001

1-(3-(4, 6-d i heny 1 pyr imidi n— 2_y 1 ) pheny 1 ) -6- (2~ni tr opheny 1 ) - IH- i ndo 1 e의 합성 Synthesis of 1- (3- (4, 6-di heny 1 pyr imidi n— 2_y 1) pheny 1) -6- (2 ~ ni tr opheny 1)-IH- i ndo 1 e

Figure imgf000125_0002
Figure imgf000125_0002

2- ( 3- ch 1 or opheny 1 ) - , 6-d i pheny 1-1,3,5-triazine 대신 2-(3-chloro pheny 0-4， 6-d i pheny lpyri mi dine올 사용하는 것을 제외하고는 상기 준비예 28의 2- (3- ch 1 or opheny 1)-, except for using 2- (3-chloro pheny 0-4, 6-di pheny lpyri mi dine instead of 6-di pheny 1-1,3,5-triazine Of Preparation Example 28

<단계 1>과 동일한 과정을 수행하여 1一 ( 3一 ( 4， 6-d i heny 1 yr imidi η-2-y 1 ) pheny 1 ) -6- (2-ni tr opheny 1 )一 IH— i ndo 1 e을 얻었다. Follow the same procedure as in <Step 1> to make 1 1 (3 一 (4 ， 6-di heny 1 yr imidi η-2-y 1) pheny 1) -6- (2-ni tr opheny 1) 一 IH— i ndo 1 e was obtained.

GC-Mass (이론치: 544.19 g/mol, 측정치: 544 g/mol)  GC-Mass (Theoretical value: 544.19 g / mol, Measured value: 544 g / mol)

<단계 2> IC-29의 합성 <Step 2> Synthesis of IC-29

Figure imgf000126_0001
Figure imgf000126_0001

5- (2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 1-(3-(4, 6-d i heny 1 pyr imidi -2-y 1 ) heny 1)一 6一(2— nitr opheny l)-lH-i ndo 1 e을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-29을 얻었다.  5- (2-nitr opheny 1) -1-pheny 1-IH-i ndo 1 e instead of 1- (3- (4, 6-di heny 1 pyr imidi -2-y 1) obtained in <Step 1> heny 1) 一 6 一 (2—nitr opheny l) -lH-i ndo 1 e except that using the same process as in <step 4> of Preparation Example 1 to obtain the IC-29.

GC-Mass (이론치 : 512.20 g/mol, 측정치 : 512 g/mol)  GC-Mass (Theoretical value: 512.20 g / mol, Measured value: 512 g / mol)

[준비예 30] IC-30의 합성 Preparation Example 30 Synthesis of IC-30

Figure imgf000126_0002
Figure imgf000126_0002

1一 ( 3一 ( 4 , 6—d i pheny 1-1,3, 5~triazi η-2-y 1 ) pheny 1 )-5-(2-ni t r opheny 1 )-lH-i ndo 1 e의 합성 1 一 (3 一 (4, 6—di pheny 1-1,3, 5 to triazi η-2-y 1) pheny 1) -5- (2-ni tr opheny 1) -lH-i ndo 1 e synthesis

Figure imgf000126_0003
Figure imgf000126_0003

6- ( 2-n i t r opheny 1 ) - IH- i ndo 1 e 대신 5-(2-ni trophenyl )-lH-indole을 사용하는 제외하고는 상기 준비예 28의 <단계 1〉과 동일한 과정을 수행하여 11- ( 3- ( 4 , 6-d i pheny 1 - 1 , 3 , 5- 1 r i az i η-2-y 1 ) pheny 1 ) -5- ( 2-n i t r o pheny 1 ) - 1H- i ndo I e을 얻었다. 6- (2-nitr opheny 1)-The same procedure as in <Step 1> of Preparation Example 28 was performed except that 5- (2-ni trophenyl) -lH-indole was used instead of IH- i ndo 1 e. 11- (3- (4, 6-di pheny 1-1, 3, 5- 1 ri az i η-2-y 1) pheny 1) -5- (2-nitro pheny 1)-1H- i ndo I e was obtained.

GC-Mass (이론치 : 545.19 g/mol, 측정치: 545 g/raol)  GC-Mass (Theoretical value: 545.19 g / mol, Measured value: 545 g / raol)

<단계 2> IC-30의 합성  <Step 2> Synthesis of IC-30

Figure imgf000127_0001
Figure imgf000127_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 <단계 1>에서 얻은 ll-(3-(4,6-di henyl-l,3,5-tr iazin-2-yl ) phenyl )-5-(2-ni tro phenyl ) 1Hᅳ indole을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-30을 얻었다.  Ll- (3- (4,6-di henyl-l, 3,5-tr iazin obtained in <Step 1> instead of 5- (2-nitr opheny 1)-1-pheny 1-1H- i ndo 1 e IC-30 was obtained by the same procedure as <Step 4> of Preparation Example 1, except that 2-yl) phenyl) -5- (2-nitrophenyl) 1H ᅳ indole was used.

GC-Mass (이론치: 513.20 g/mol, 축정치: 513 g/mol)  GC-Mass (Theoretical value: 513.20 g / mol, Accumulated value: 513 g / mol)

[준비예 31] IC-31의 합성 Preparation Example 31 Synthesis of IC-31

Figure imgf000127_0002
Figure imgf000127_0002

1-(3-(4, 6-d i pheny lpyrimidi n~2-y 1 ) pheny 1 )一5一 ( 2—n i t r opheny I ) _ 1H— i ndo 1 e의 합성 Synthesis of 1- (3- (4, 6-di pheny lpyrimidi n ~ 2-y 1) pheny 1) 一 5 一 (2—nitr opheny I) _ 1H— i ndo 1 e

Figure imgf000128_0001
Figure imgf000128_0001

6一 ( 2-n i t r opheny 1 ) - IH一 i ndo 1 e과  6 一 (2-n i t r opheny 1)-IH 一 i ndo 1 e and

2—(3—chl oropheny 1 )-4,6-di henyl-l,3,5-triazine 대신 5ᅳ (2一 ni trophenyl )—1Η一 indole과 2_(3ᅳ chloro phenyl )-4,6-diphenylpyr imidine-¾- 사용하는 것을 제외하고는 상기 준비예 28의 <단계 1>과 동일한 과정을 수행하여 1- ( 3- ( 416~d i pheny 1 yr i m i d i η-2-y 1 ) pheny 1 )-5-(2-ni trophenyl ) 1Hᅳ indole을 얻었다. 5 ᅳ (2 一 ni trophenyl) —1Η 一 indole and 2_ (3 ᅳ chloro phenyl) -4,6- instead of 2— (3—chl oropheny 1) -4,6-di henyl-l, 3,5-triazine Except for using diphenylpyr imidine-¾- 1- (3- (4 1 6 ~ di pheny 1 yr imidi η-2-y 1) pheny 1 ) -5- (2-ni trophenyl) 1H ᅳ indole was obtained.

GC-Mass (이론치: 544.19 g/mol, 측정치: 544 g/mol)  GC-Mass (Theoretical value: 544.19 g / mol, Measured value: 544 g / mol)

<단계 2> IC-31의 합성  <Step 2> Synthesis of IC-31

Figure imgf000128_0002
Figure imgf000128_0002

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - IH- i ndo 1 e 대신 상기 <단계 1>에서 얻은 l-(3-(4,6-di heny 1 yr iraidi η-2-y 1 ) heny l)-5-(2-nitr opheny 1 ) - IH- i ndo 1 e을 사용하는 것을 제외하고는 상기 준비예 1의 <단계 4>과 동일한 과정을 수행하여 IC-31을 얻었다. 5- (2-nitr opheny 1)-l- (3- (4,6-di heny 1 yr iraidi η-2-y 1 obtained in <Step 1> instead of 1-pheny 1 -IH-i ndo 1 e ) Heny l) -5- (2-nitr opheny 1)-IH- i ndo 1 e except for using the same process as in <Step 4> of Preparation Example 1 IC-31 was obtained.

GC-Mass (이론치: 512.20 g/raol, 측정치: 512 g/mol)  GC-Mass (Theoretical value: 512.20 g / raol, Measured value: 512 g / mol)

[합성예 1] In l의 합성  Synthesis Example 1 Synthesis of In l

Figure imgf000129_0001
Figure imgf000129_0001

질소 기류 하에서 준비예 1에서 제조한 일 화합물인 IC-la(5g, 17.71 mmol), 2-br omo-4 , 6-d i pheny 1 yr i d i ne ( 8.24 g, 26.56薩 ol), Cu powder (0.11 g'.1.77 mmo 1 ) , 2C03(2.44 g, 17.71 mmol), Na2S04(2.52 g, 17.71 mmol) 및 nitrobenzene (100 ml)를 흔합하고 190°C에서 12시간동안 교반하였다. IC-la (5 g, 17.71 mmol), 2-br omo-4, 6-di pheny 1 yr idi ne (8.24 g, 26.56 μl), Cu powder (0.11), which is a compound prepared in Preparation Example 1, under nitrogen stream g'.1.77 mmo 1), 2C0 3 (2.44 g, 17.71 mmol), Na 2 S0 4 (2.52 g, 17.71 mmol) and nitrobenzene (100 ml) were combined and stirred at 190 ° C for 12 h.

반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgS04를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:MC = 1:1 (v/v))로 정제하여 목적 화합물인 Inv-1(6.25 g, 수율 69%)을 얻었다. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 . After removing the solvent of the organic layer was purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to give the title compound Inv-1 (6.25 g, 69% yield).

GC-Mass (이론치: 511.20 g/mol, 측정치: 511 g/raol)  GC-Mass (Theoretical value: 511.20 g / mol, Measured value: 511 g / raol)

[합성예 2] Inv-2의 합성  Synthesis Example 2 Synthesis of Inv-2

Figure imgf000129_0002
Figure imgf000129_0002

2-br omo-4 , 6~d i pheny 1 pyr i d i ne 대신 6ᅳ brom으 2，3'ᅳ bipyridine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-2(5.02 g, 수율 65%)을 얻었다. 6br brom 2，3 'di bipyridine instead of 2-br omo-4, 6 ~ di pheny 1 pyr idi ne Except for that, the same procedure as in Synthesis Example 1 was carried out to obtain Inv-2 (5.02 g, yield 65%) as a target compound.

GC-Mass (이론치 : 436.17 g/mol， 측정치: 436 g/mol)  GC-Mass (Theoretical value: 436.17 g / mol, Measured value: 436 g / mol)

[합성예 3] Inv_3의 합성  Synthesis Example 3 Synthesis of Inv_3

Figure imgf000130_0001
Figure imgf000130_0001

IC-la 대신 준비예 1에서 제조한 또 다른 화합물인 IC-lb를 사용하고 2-bromo-4， 6-d i pheny 1 pyr idine 대신 2-bromo~4 , 6一 d i phenyl -1 , 3,5-triazi ne를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-3(3.91 g, 수율 43«을 얻었다. Use IC-lb, another compound prepared in Preparation Example 1 instead of IC-la, and replace 2-bromo-4, 6-di pheny 1 pyr idine with 2-bromo ~ 4, 6 一 diphenyl-1, 3,5 Except for using -triazi ne was carried out the same procedure as in Synthesis Example 1 to obtain the target compound Inv-3 (3.91 g, yield 43 «.

GC-Mass (이론치: 513.20g/mol, 측정치 : 513 g/mol)  GC-Mass (Theoretical value: 513.20 g / mol, Measured value: 513 g / mol)

[합성예 4] Inv-4의 합성  Synthesis Example 4 Synthesis of Inv-4

Figure imgf000130_0002
Figure imgf000130_0002

IC-la 대신 준비예 1에서 제조한 또다른 화합물인 IC-lb을 사용하고 2-br omo-4 , 6-d i pheny 1 pyr idine 대신 4-bromodibenzo [b,d]thiophene를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-4(5.02 g, 수율 61¾»)를 얻었다. GC-Mass (이론치 : 464.13 g/mol, 측정치 : 464 g/mol) Except for using IC-lb, another compound prepared in Preparation Example 1 instead of IC-la, and 4-bromodibenzo [b, d] thiophene instead of 2-br omo-4, 6-di pheny 1 pyr idine Was carried out in the same manner as in Synthesis example 1 to obtain Inv-4 (5.02 g, yield 61¾ ») as a target compound. GC-Mass (Theoretical value: 464.13 g / mol, Measured value: 464 g / mol)

[합성예 5] Inv5의 합성  Synthesis Example 5 Synthesis of Inv5

Figure imgf000131_0001
Figure imgf000131_0001

IC-la 대신 준비예 2에서 제조한 Prepared in Preparation Example 2 instead of IC-la

3一 phenyl一 3,6一 dihydropyrrolo[2,3—c]carbazole을 사용하고 2ᅳ brom으 4,6ᅳ di phenyl pyridine 대신 2ᅳ bromo-4,6ᅳ diphenylpyr imidine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정올 수행하여 목적 화합물인 Inv-5(5.36 g, 수을 59%)를 얻었다. Synthesis except using 3 一 phenyl 一 3,6 一 dihydropyrrolo [2,3—c] carbazole and 2azole bromo-4,6-4 diphenylpyr imidine instead of 4 ᅳ 6 phenyl pyridine for 2 ᅳ brom In the same manner as in Example 1, Inv-5 (5.36 g, 59%) was obtained as a target compound.

GC-Mass (이론치: 512.20 g/mol, 측정치: 512 g/mol)  GC-Mass (Theoretical value: 512.20 g / mol, Measured value: 512 g / mol)

[합성예 6] Inv-6의 합성  Synthesis Example 6 Synthesis of Inv-6

Figure imgf000131_0002
Figure imgf000131_0002

IC-la 대신 준비예 2에서 제조한 Prepared in Preparation Example 2 instead of IC-la

3-phenyl-3 , 6-d i hydropyrrol o[2, 3_c Jcarbazo 1 e을 사용하고3-phenyl-3, 6-d i hydropyrrol o [2, 3_c Jcarbazo 1 e

2-br omo-4 , 6-d i pheny 1 pyr i d i ne 대신 3ᅳ brom으 9-phenylᅳ 9H carbazole을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-6(6.58 g, 수율 71%)를 얻었다. Except for using 9-phenyl ᅳ 9H carbazole as 3 ᅳ brom instead of 2-br omo-4 and 6-di pheny 1 pyr idi ne, Inv-6 (6.58) g, Yield 71%).

GC-Mass (이론치: 523.20 g/mol, 측정치: 523 g/mol)  GC-Mass (Theoretical value: 523.20 g / mol, Measured value: 523 g / mol)

[합성예 7] Inv-7의 합성  Synthesis Example 7 Synthesis of Inv-7

Figure imgf000132_0001
Figure imgf000132_0001

IC-la 대신 준비예 3에서 제조한 l-pheny 1-1, 6一 d i hydropyr rolo[3, 2ᅳ c lcarbazol e을 사용하고 Instead of IC-la, l-pheny 1-1, 6 一 d i hydropyr rolo [3, 2 ᅳ c lcarbazol e prepared in Preparation Example 3 was used.

2-br omo-4 , 6-d i heny 1 pyr i d i ne 대신 4-brom으 N,N-diphenylani line을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Invᅳ 7(6.8 g, 수율 73%)를 얻었다. Except for using N, N-diphenylani line as 4-brom instead of 2-br omo-4 and 6-di heny 1 pyr idi ne, the same procedure as in Synthesis Example 1 was carried out to obtain Inv ᅳ 7 (6.8). g, yield 73%).

GC-Mass (이론치 : 525.22 g/mol , 측정치 : 525 g/mol)  GC-Mass (Theoretical value: 525.22 g / mol, Measured value: 525 g / mol)

[합성예 8] Inv-8의 합성  Synthesis Example 8 Synthesis of Inv-8

Figure imgf000132_0002
Figure imgf000132_0002

nitrobenzene  nitrobenzene

IC-la 대신 준비예 3에서 제조한 l-pheny 1-1,6-dihydropyrrolo [3, 2-c] car bazole^- 사용하고 2-br omo-4 , 6-d i pheny 1 pyr i d i ne 대신 5~br omo-2-pheny 1 pyr i m i d i ne¾- 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-8(3.48 g, 수을 45%)를 얻었다. Instead of IC-la, l-pheny 1-1,6-dihydropyrrolo [3, 2-c] car bazole ^-prepared in Preparation Example 3 was used and 2-br omo-4, 6-di pheny 1 pyr idi ne was used instead of 5 ~ br omo-2-pheny 1 pyr imidi ne¾- except for using by performing the same procedure as in synthesis example 1, the desired compound of Inv-8 (3.48 g, sueul 45%).

GC-Mass (이론치 : 436.17 g/mol , 측정치: 436 g/mol)  GC-Mass (Theoretical value: 436.17 g / mol, Measured value: 436 g / mol)

[합성예 9] Inv-9의 합성  Synthesis Example 9 Synthesis of Inv-9

Figure imgf000133_0001
Figure imgf000133_0001

IC-la 대신 준비예 4에서 제조한 일 화합물인 IC-4a을 사용하고 2-br omo-4 , 6-d i pheny 1 pyr i d i e 대신 2一(4一 brotnophenyl)pyridine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-9(4.97 g, 수율 68%)를 얻었다.  Synthesis except for using IC-4a, a compound prepared in Preparation Example 4 instead of IC-la, and 2 一 (4 一 brotnophenyl) pyridine instead of 2-br omo-4, 6-di pheny 1 pyr idie Inv-9 (4.97 g, yield 68%) was obtained by the same procedure as in Example 1.

GC-Mass (이론치: 485.19 g/mol, 측정치: 485 g/mol)  GC-Mass (Theoretical value: 485.19 g / mol, Measured value: 485 g / mol)

[합성예 10] Irn^lO의 합성  Synthesis Example 10 Synthesis of Irn ^ O

Figure imgf000133_0002
Figure imgf000133_0002

IC-la 대신 준비예 4에서 제조한 일 화합물인 IC-4a을 사용하고 2-bromo~4 ,6-di pheny lpyr idine 대신 4ᅳ br omo-2- (pyridin-3-yl) pyr i m i d i ne을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인Instead of IC-la, one compound (IC-4a) prepared in Preparation Example 4 was used, and 4 2- br omo-2- (pyridin-3-yl) pyr imidi ne was substituted for 2-bromo to 4,6-di pheny lpyr idine. Except for using the same process as in Synthesis Example 1

Inv-10(3.08 g, 수율 42%)를 얻었다. GC-Mass (이론치: 487.18 g/mol, 즉정치: 487 g/mol) Inv-10 (3.08 g, yield 42%) was obtained. GC-Mass (Theoretical value: 487.18 g / mol, Immediate: 487 g / mol)

[합성예 11] Inv-11의 합성  Synthesis Example 11 Synthesis of Inv-11

Figure imgf000134_0001
Figure imgf000134_0001

IC-la 대신 준비예 4에서 제조한 또 다른 화합물인 IC 4b을 사용하고 2-bromo-4 , 6 d i pheny 1 pyr idine 대신 3,3'-( 5-bromo- 1 , 3 pheny 1 ene ) d i pyr i d i ne을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-ll(5.08 g, 수율 60%)를 얻었다.  Instead of IC-la, another compound prepared in Preparation Example 4, IC 4b, was used, and instead of 2-bromo-4, 6 di pheny 1 pyr idine, 3,3 '-(5-bromo-1, 3 pheny 1 ene) di Inv-ll (5.08 g, yield 60%) was obtained by the same procedure as in Synthesis Example 1, except that pyr idi ne was used.

GC-Mass (이론치: 562.22 g/mol, 측정치: 562 g/mol)  GC-Mass (Theoretical value: 562.22 g / mol, Measured value: 562 g / mol)

[합성예 12] I r 2의 합성  Synthesis Example 12 Synthesis of I r 2

Figure imgf000134_0002
Figure imgf000134_0002

IC-la 대신 준비예 4에서 제조한 또 다른 화합물인 IC-4b를 사용하고 2-br omo-4 , 6-d i pheny 1 py r i d i ne 대신 4-(4-bromophenyl)-3,5-diplienyl-4H-l,2,4-triazole을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv- 12(4.91 g, 수율 52%)를 얻었다. Instead of IC-la, another compound prepared in Preparation Example 4, IC-4b, was used, and 4- (4-bromophenyl) -3,5-diplienyl- instead of 2-br omo-4, 6-di pheny 1 py ridi ne. Except for using 4H-1,2,4-triazole, Inv-12 (4.91 g, 52% yield) was obtained in the same manner as in Synthesis Example 1. Got it.

GC-Mass (이론치: 627.24 g/mol, 측정치: 627 g/mol)  GC-Mass (Theoretical value: 627.24 g / mol, Measured value: 627 g / mol)

[합성예 13] Inv-13의 합성  Synthesis Example 13 Synthesis of Inv-13

Figure imgf000135_0001
Figure imgf000135_0001

IC-la 대신 준비예 5에서 제조한 일 화합물인 IC-5a을 사용하고 Instead of IC-la, one compound IC-5a prepared in Preparation Example 5 was used.

2-br omo-4 , 6~d i pheny 1 pyr i d i ne 대신2-br omo-4, 6 ~ di pheny 1 pyr idi ne instead

2-(4-bromophenyl)-4,6-diphenylᅳ 1,3,5-triazine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-13(6.06 g, 수율 63%)를 얻었다. Except for using 2- (4-bromophenyl) -4,6-diphenyl ᅳ 1,3,5-triazine, the same procedure as in Synthesis Example 1 was carried out to provide Inv-13 (6.06 g, 63% yield). )

GC-Mass (이론치: 639.24 g/mol, 측정치: 639 g/mol)  GC-Mass (Theoretical value: 639.24 g / mol, Measured value: 639 g / mol)

[합성예 14] Inv-14의 합성  Synthesis Example 14 Synthesis of Inv-14

Figure imgf000135_0002
Figure imgf000135_0002

대신 준비예 5에서 . 제조한 일 화합물인 IC-5a을 사용하고 2-br omo-4 , 6-d i pheny 1 pyr i d i ne 대신 2 ' -br omo~3 , 4 ' -b i pyr i d i ne-§- 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv— 14(5.05 g, 수율 69%)를 얻었다. In Preparation Example 5 instead. Using IC-5a, a compound prepared Except for using 2-br omo-4, 6-di pheny 1 pyr idi ne, the same procedure as in Synthesis Example 1 was performed except that 2 '-br omo ~ 3, 4' -bi pyr idi ne-§- was used. The compound Inv-14 (5.05 g, 69% yield) was obtained.

GC-Mass (이론치: 486.18 g/mol, 축정치: 486 g/mol)  GC-Mass (Theoretical value: 486.18 g / mol, Accumulated value: 486 g / mol)

[합성예 15] Inv-15의 합성  Synthesis Example 15 Synthesis of Inv-15

Figure imgf000136_0001
Figure imgf000136_0001

대신 준비예 5에서 제조한 또다른 화합물인 IC-5b을 사용하고

Figure imgf000136_0002
Instead using another compound prepared in Preparation Example 5 IC-5b
Figure imgf000136_0002

2— (4ᅳ bromophenyl )-l-phenyl-lHᅳ benzo[d] imidazole을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-15(4.34 g, 수율 48%)를 얻었다.  2— (4 ᅳ bromophenyl) -l-phenyl-lH ᅳ benzo [d] The same procedure as in Synthesis Example 1 was conducted except that the target compound Inv-15 (4.34 g, yield 48%) was obtained. Got it.

GC-Mass (이론치: 600.23 g/mol, 측정치: 600 g/mol)  GC-Mass (Theoretical value: 600.23 g / mol, Measured value: 600 g / mol)

[합성예 16] Inv~16의 합성  Synthesis Example 16 Synthesis of Inv ~ 16

Figure imgf000136_0003
IC-la 대신 준비예 5에서 제조한 또다른 화합물인 IC— 5b을 사용하고 2一 bran으 4 ,6-di pheny 1 pyridine 대신 2-( 4ᅳ br omopheny 1 )-4,6-di pheny 1 pyr i m i d i ne을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-16(4.13 g, 수율 43%)를 얻었다.
Figure imgf000136_0003
Instead of IC-la, another compound prepared in Preparation Example 5, IC-5b, was used, and 2- (4 一 br omopheny 1) -4,6-di pheny 1 was used instead of 2, 4,6-di pheny 1 pyridine. Except for using pyr imidi ne was carried out the same procedure as in Synthesis Example 1 to obtain the target compound Inv-16 (4.13 g, 43% yield).

GC-Mass (이론치 : 638.25 g/mol 측정치: 638 g/mol)  GC-Mass (Theoretical value: 638.25 g / mol Measured value: 638 g / mol)

[합성예 17] Inv-17의 합성  Synthesis Example 17 Synthesis of Inv-17

Figure imgf000137_0001
Figure imgf000137_0001

질소 기류 하에서 준비예 6에서 제조한 일 화합물인 IC-6a(5g, 13.84隱 ol), Iodobenzene(4.24 g, 20.76 mmol), Cu powder (0.09 g, 1.38 mmol), K2C03(1.91 g, 13.84 醒 ol), Na2S04(1.97 g, 13.84 mmol) 및 ni trobenzene(80 ml)을 흔합하고 190°C에서 12시간 동안 교반하였다. 반웅이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgS04를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:MC = 5:1 (v/v))로 정제하여 중간 화합물인 6-bromo-l,9-diphenyl-l,9-dihydropyrrolo[2,3-b]carbazole (3.45 g, 수율 57%)을 얻었다. IC-6a (5 g, 13.84 μl), Iodobenzene (4.24 g, 20.76 mmol), Cu powder (0.09 g, 1.38 mmol), K 2 CO 3 (1.91 g, 13.84 dl ol), Na 2 S0 4 (1.97 g, 13.84 mmol) and ni trobenzene (80 ml) were combined and stirred at 190 ° C for 12 h. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 . After removing the solvent of the organic layer and purified by column chromatography (Hexane: MC = 5: 1 (v / v)) to the intermediate compound 6-bromo-l, 9-diphenyl-l, 9-dihydropyrrolo [2,3-b ] carbazole (3.45 g, yield 57%) was obtained.

질소 기류 하에서， 얻어진 상기 중간 물질 (3.45 g, 7.89 画 ol), 2,3'-bipyridin-6-ylboronic acid(1.89 g, 9.47隱 ol), NaOH(0.95 g, 23.67 mmol) 및 THF/H20(100 ml/50 ml)를 흔합하여 교반한 다음， 40°C에서 0.46 g (5 mol%)의 Pd(PPh3)4를 넣고 80°C에서 12시간 동안 교반하였다. 반웅이 종결된 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 여과하였다. 얻어진 유기층의 용매를 제거한후 컬럼 크로마토그래피 (Hexane:EA = 3:1 (v/v))로 정제하여 목적 화합물인 Inv-17(3.36 g, 수율 83¾>)을 얻었다. The intermediate obtained (3.45 g, 7.89 画 ol), 2,3'-bipyridin-6-ylboronic acid (1.89 g, 9.47 隱 ol), NaOH (0.95 g, 23.67 mmol) and THF / H 2 0 Insert a (100 ml / 50 ml) were combined and then a common stirring, Pd (PPh 3) 4 at 40 ° C 0.46 g (5 mol %) was stirred at 80 ° C for 12 hours. After the reaction Extracted with methylene chloride, MgS0 4 was added and filtered. After removing the solvent of the obtained organic layer was purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to give the title compound Inv-17 (3.36 g, yield 83¾>).

GC-Mass (이론치: 512.20 g/mol, 측정치: 512 g/mol)  GC-Mass (Theoretical value: 512.20 g / mol, Measured value: 512 g / mol)

[합성예 18] Inv-18의 합성  Synthesis Example 18 Synthesis of Inv-18

Figure imgf000138_0001
Figure imgf000138_0001

합성예 17과 동일한 과정올 수행하되， lodobenzene 대신 3-bromoquinol ine을 사용하여 증간 화합물인 The same procedure as in Synthesis Example 17 was carried out except that 3-bromoquinol ine was used instead of lodobenzene

6-br omo- 1-pheny 1 -9- ( qu i no 1 in-2-yl )-l,9-dihydropyrrolo[2,3-b]carbazole^- 얻고 2,3'-bipyr idin-6-ylboronic acid 대신 6-pheny 1 pyr i d i η-3-y 1 boron i c acidl 사용하여 목적 화합물인 Irw-18(2.63 g, 수율 76%)올 얻었다. 6-br omo- 1-pheny 1 -9- (qu i no 1 in-2-yl) -l, 9-dihydropyrrolo [2,3-b] carbazole ^-obtain 2,3'-bipyr idin-6- Instead of ylboronic acid, 6-pheny 1 pyr idi η-3-y 1 boron ic acidl was used to obtain the title compound Irw-18 (2.63 g, yield 76%).

GC-Mass (이론치: 562.22 g/mol, 측정치: 562 g/mol)  GC-Mass (Theoretical value: 562.22 g / mol, Measured value: 562 g / mol)

[합성예 19] 의 합성  Synthesis of Synthesis Example 19

Figure imgf000138_0002
Figure imgf000138_0002

합성예 17과 동일한 과정을 수행하되， IC-6a 대신 준비예 6에서 제조한 또 화합물인 IC-6b을 사용하여 중간 화합물인 그 bromo一 3， 10-d i pheny 1ᅳ 3， 10-dihydropyrrol o[3, 2ᅳ a] car bazo 1 e을 얻고， The same procedure as in Synthesis Example 17 was performed, except that IC-6b was used instead of IC-6a, and another compound prepared in Preparation Example 6 was used as an intermediate compound, bromo 一 3, 10-di pheny 1 ᅳ 3 and 10-dihydropyrrol o [ 3, 2 ᅳ a] car bazo 1 e,

2,3'-bi yridin-6-ylboronic acid 대신 4 , 6-d i heny 1 pyr i d i η-2-y 1 bor on i c acidi 사용하여 목적 화합물인 Inv-19(3.1 g, 수율 77%)을 얻었다. 4, 6-di heny 1 pyr idi η-2-y 1 bor on ic acidi instead of 2,3'-bi yridin-6-ylboronic acid Inv-19 (3.1 g, yield 77%) was obtained using the target compound.

GC-Mass (이론치 : 587.24 g/raol, 측정치 : 587 g/mol)  GC-Mass (Theoretical value: 587.24 g / raol, Measured value: 587 g / mol)

[합성예 20] Inv-20의 합성  Synthesis Example 20 Synthesis of Inv-20

Figure imgf000139_0001
Figure imgf000139_0001

합성예 17과 동일한 과정을 수행하되， IC-6a 대신 준비예 6에서 제조한 또다른 화합물인 IC-6b를 사용하고 Iodobenzene 대신 l-bromo-3,5-di phenyl benzene을 사용하여 중간 화합물을 얻고, 2,3'-bipyridin-6-ylboronic acid 대신 4-(pyridin-3-yl)phenylboronic acid를사용하여 목적 화합물인 Inv-20(2.67 g,수율 79%)을 얻었다.  Performing the same process as in Synthesis Example 17, using another compound prepared in Preparation Example 6 instead of IC-6a IC-6b and l-bromo-3,5-di phenyl benzene instead of Iodobenzene to obtain an intermediate compound 4- (pyridin-3-yl) phenylboronic acid was used instead of 2,3'-bipyridin-6-ylboronic acid to obtain Inv-20 (2.67 g, yield 79%).

GC-Mass (이론치: 663.27 g/mol, 측정치: 663 g/mol)  GC-Mass (Theoretical value: 663.27 g / mol, Measured value: 663 g / mol)

[합성예 21] Inv~21의 합성  Synthesis Example 21 Synthesis of Inv ~ 21

Figure imgf000139_0002
Figure imgf000139_0002

IC-la 대신 준비예 8에서 제조한 Prepared in Preparation Example 8 instead of IC-la

1- ( 4 , 6~d i pheny 1 py r i d i η-2-y 1 )-l,9-dihydropyrrolo[2,3-b]carbazole^- 사용하고1- (4, 6 ~ di pheny 1 py ridi η-2-y 1) -l, 9-dihydropyrrolo [2,3-b] carbazole ^-

2- br omo-4 , 6-d i pheny 1 py r i d i ne 대신 3~br omo-9-pheny 1 -9H-car bazo 1 e 사용하는 것을 제외하고는 합성예 1과동일한과정을 수행하여 목적 화합물인 w-21(2.84 g, 수율 6 )를 얻었다. GC-Mass (이론치: 676.26 g/mol, 측정치: 676 g/mol) 2- br by omo-4, 6-di pheny 1 except that instead of using py ridi ne 3 ~ br omo-9-pheny 1 -9H-car bazo 1 e performs the same process as in Synthesis Example 1 of the aimed compound w-21 (2.84 g, yield 6) was obtained. GC-Mass (Theoretical value: 676.26 g / mol, Measured value: 676 g / mol)

[합성예 22] Inv-22의 합성  Synthesis Example 22 Synthesis of Inv-22

Figure imgf000140_0001
Figure imgf000140_0001

IC-la 대신 준비예 8에서 제조한 Prepared in Preparation Example 8 instead of IC-la

1- (4, 6-di pheny lpyridin-2-yl)-l,9-dihydropyrrolo[2,3-b]carbazole-i- 사용하고1- (4, 6-di pheny lpyridin-2-yl) -l, 9-dihydropyrrolo [2,3-b] carbazole-i-

2- br omo-4 , 6~d i pheny 1 pyr i d i ne 대신 2- ( 4-br omopheny 1 ) pyr i d i ne^- 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-22(2.64 g, 수율 65%)를 얻었다. Except for using 2- (4-br omopheny 1) pyr idi ne ^-in place of 2- br omo-4, 6 ~ di pheny 1 pyr idi ne 22 (2.64 g, yield 65%) was obtained.

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[합성예 23] Inv-23의 합성  Synthesis Example 23 Synthesis of Inv-23

Figure imgf000140_0002
Figure imgf000140_0002

IC-la 대신 준비예 7에서 제조한 Prepared in Preparation Example 7 instead of IC-la

3- ( 4 , 6-d i pheny 1 pyr i d i η-2-y 1 )-3, 10-dihydropyrrolo[3,2-a]carbazole-i: 사용하고 2-br omo-4 , 6-d i pheny 1 py r i d i ne 대신 3ᅳ bromo-9-(4,6-diphenylpyridin-2-yl)-9H-carbazole을 사용하는 것을 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-23(2.74 g, 수을

Figure imgf000141_0001
얻었다. 3- (4, 6-di pheny 1 pyr idi η-2-y 1) -3, 10-dihydropyrrolo [3,2-a] carbazole-i: use 2-br omo-4, 6-di pheny 1 instead of py ridi ne 3 ᅳ bromo-9- (4,6-diphenylpyridin-2-yl) -9H-carbazole was subjected to the same procedure as in Synthesis Example 1 to obtain Inv-23 (2.74 g, number) as a target compound.
Figure imgf000141_0001
Got it.

GC-Mass (이론치: 829.32 g/mol, 측정치: 829 g/mol)  GC-Mass (Theoretical value: 829.32 g / mol, Measured value: 829 g / mol)

[합성예 24] Inv-24의 합성  Synthesis Example 24 Synthesis of Inv-24

Figure imgf000141_0002
Figure imgf000141_0002

IC-la 대신 준비예 7에서 제조한 Prepared in Preparation Example 7 instead of IC-la

3-(4,6-diphenylpyridin-2ᅳ yl)-3,10-dihydropyrrolo[3,2-a]carbazole을 사용하고 2-bromo-4 , 6~di pheny 1 pyr i di ne 대신 4-bromobi phenyl을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-24(2.83 g, 수율 70%)를 얻었다. 3- (4,6-diphenylpyridin-2 ᅳ yl) -3,10-dihydropyrrolo [3,2-a] carbazole and 4-bromobi phenyl instead of 2-bromo-4, 6 to di pheny 1 pyr i di ne Except for using the same procedure as in Synthesis Example 1 to obtain the title compound Inv-24 (2.83 g, yield 70%).

GC-Mass (이론치: 587.24 g/mol, 측정치: 587 g/mol)  GC-Mass (Theoretical value: 587.24 g / mol, Measured value: 587 g / mol)

[합성예 25] Inv^25의 합성  Synthesis Example 25 Synthesis of Inv ^ 25

Figure imgf000141_0003
Figure imgf000141_0003

대신 준비예 9에서 제조한 3-(2，3'-^ ^(1 1ᅳ6- 1)-3，6ᅳ(111^(1 1 )10[2，3ᅳ(;]031 32016을 사용하고Manufactured in Preparation Example 9 3- (2,3 '-^ ^ (1 1 ᅳ 6- 1) -3,6 ᅳ (111 ^ (1 1) 10 [2，3 ᅳ (;] 031 32016

2-bromo~4 , 6-d i pheny 1 pyr idine 대신 2-bromo~4 , 6-d i pheny 1 _ 1， 3， 5ᅳ t r i az i ne을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-25(2.12 g, 수율 43%)를 얻었다. Except for using 2-bromo ~ 4, 6-di pheny 1 _ 1, 3, 5 ᅳ tri az i ne instead of 2-bromo ~ 4, 6-di pheny 1 pyr idine The desired compound Inv-25 (2.12 g, yield 43%) was obtained.

GC-Mass (이론치: 591.22 g/mol, 측정치: 591 g/mol)  GC-Mass (Theoretical value: 591.22 g / mol, Measured value: 591 g / mol)

[합성예 26] Inv-26의 합성  Synthesis Example 26 Synthesis of Inv-26

Figure imgf000142_0001
Figure imgf000142_0001

IC-la 대신 준비예 9에서 제조한 Prepared in Preparation Example 9 instead of IC-la

3-(2,3'-bipyridi η-6-y 1 ) -3， 6-d i hydropyrrol o[2,3-c ] car bazo 1 e을 사용하고3- (2,3'-bipyridi η-6-y 1) -3, 6-d i hydropyrrol o [2,3-c] car bazo 1 e

2-br omo-4 , 6-d i pheny 1 pyr idine 대신 5ᅳ bromo-2,2'ᅳ bipyridine을 사용하는 것을 제외하고는 합성예 1과동일한과정을 수행하여 목적 화합물인 Inv-26(2.23 g, 수율 52%)를 얻었다. Except for using 52 bromo-2,2 'ᅳ bipyridine instead of 2-br omo-4 and 6-di pheny 1 pyr idine, the same procedure as in Synthesis Example 1 was carried out to obtain Inv-26 (2.23 g). , Yield 52%) was obtained.

GC-Mass (이론치: 514.19 g/mol, 측정치: 514 g/mol)  GC-Mass (Theoretical value: 514.19 g / mol, Measured value: 514 g / mol)

[합성예 27] Inv-27의 합성  Synthesis Example 27 Synthesis of Inv-27

Figure imgf000142_0002
질소 기류 하에서 IC-la (3 g, 10.63画 ol), 3-bromobi phenyl (3.72 g, 15.94 mmol), Cu powder (0.07 g, 1.06 mmol), 2C03 (1.47 g, 10.63 mmol), Na2S04 (1.51 g, 10.63麵 ol), nitrobenzene (100 ml)를 혼합하고 200°C에서 24시간 동안교반하였다. 반응 종결 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리하여 MgS04를 사용하여 물을 제거하였다. 물이 제거된 유기층에서 용매를 제거한후 컬럼 크로마토그래피 (Hexane:MC = 1:1 (v/v))로 정제하여 목적 화합물인 Inv-27 (2.26 g, 수율 49 «을 얻었다.
Figure imgf000142_0002
IC-la (3 g, 10.63 μl), 3-bromobi phenyl (3.72 g, 15.94 mmol), Cu powder (0.07 g, 1.06 mmol), 2 C0 3 (1.47 g, 10.63 mmol), Na 2 SO 4 (1.51 g, 10.63 μl) and nitrobenzene (100 ml) were mixed and stirred at 200 ° C. for 24 hours. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 . After removing the solvent in the organic layer was removed from water and purified by column chromatography (Hexane: MC = 1: 1 (v / v)) to give the title compound Inv-27 (2.26 g, yield 49 «.

GC-Mass (이론치 : 434.18 g/mol, 측정치 : 434 g/mol)  GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

[합성예 28] Imr28의 합성  Synthesis Example 28 Synthesis of Imr28

Figure imgf000143_0001
Figure imgf000143_0001

lnv-28  lnv-28

3-bromobi phenyl 대신 3_(4一 bromophenyl)pyridine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 lnv-28 (2.13 g, 46 %)를 얻었다.  A target compound lnv-28 (2.13 g, 46%) was obtained in the same manner as in Synthesis Example 27, except that 3_ (4 一 bromophenyl) pyridine was used instead of 3-bromobi phenyl.

GC-Mass (이론치: 435.17 g/mol, 측정치: 435.17 g/mol)  GC-Mass (Theoretical value: 435.17 g / mol, Measured value: 435.17 g / mol)

[합성예 29] Ιη "29의 합성 Synthesis Example 29 Synthesis of Ιη29

Figure imgf000144_0001
Figure imgf000144_0001

질소 기류 하에서 IC-la (3 g, 10.63 隱 ol), 2- ( 3-ch 1 or opheny 1 ) -4 , 6-d i heny 1 -1 , 3 , 5-t r i az i ne (4.38 g, 12.75 画 ol), Pd(0Ac)2 (0.12 g, 5 mol%), NaO(t-bu) (2.04 g, 21.25 mmol), P(tᅳ bu)3 (0.21 g, 1.06 mmol) 및 Toluene (100 ml)을 흔합하고 110°C에서 12시간동안교반하였다. IC-la (3 g, 10.63 隱 ol), 2- (3-ch 1 or opheny 1) -4, 6-di heny 1 -1, 3, 5-tri az i ne (4.38 g, 12.75) under nitrogen stream画 ol), Pd (0Ac) 2 (0.12 g, 5 mol%), NaO (t-bu) (2.04 g, 21.25 mmol), P (t ᅳ bu) 3 (0.21 g, 1.06 mmol) and Toluene (100 ml) were combined and stirred at 110 ° C for 12 h.

반응이 종결된 후 에틸아세테이트로 추출한 다음 ¾¾≤04로 수분을 제거하고， 컬럼크로마토그래피 (Hexane:EA = 2:1 (v/v))로 정제하여 목적 화합물인 Inv-29 (4.89 g, 수을 78 %)을 얻었다. After the reaction was completed, the resultant was extracted with ethyl acetate, the water was removed with ¾¾≤0 4 , and purified by column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain Inv-29 (4.89 g, Number 78%).

GC-Mass (이론치: 589.23 g/mol, 측정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 30] I "30의 합성  Synthesis Example 30 Synthesis of I "30

Figure imgf000144_0002
Figure imgf000144_0002

2- ( 3-ch 1 or opheny 1 )-4, 6ᅳ d i pheny 1-1,3,5-triazine 대신 2- ( 3-ch 1 oropheny l)-4,6-di (pyr idi η-2-y 1 ) - 1， 3， 5- 1 r i az i ne을 사용하는 것을 제외하고는 상기 합성예 29와 동일한 과정을 수행하여 목적 화합물인 Inv-30 (4.97 g, 79 «를 얻었다. 2- (3-ch 1 or opheny 1) -4, 6 ᅳ di pheny 1-1,3,5-triazine instead of 2- (3-ch 1 oropheny l) -4,6-di (pyr idi η-2 -y 1)-using 1, 3, 5-1 ri az i ne Except for the title compound Inv-30 (4.97 g, 79 «) was obtained in the same manner as in Synthesis Example 29.

GC-Mass (이론치 : 591.22 g/mol, 측정치: 591 g/mol)  GC-Mass (Theoretical value: 591.22 g / mol, Measured value: 591 g / mol)

[합성예 31] Inv-31의 합성  Synthesis Example 31 Synthesis of Inv-31

Figure imgf000145_0001
Figure imgf000145_0001

3-bromob i pheny 1 대신 Instead of 3-bromob i pheny 1

2- ( 3-br omo-5-me t hy 1 pheny 1 )-4,6-di henyl-lt3,5-tr iazine^- 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-31 (3.21 g, 50 %)를 얻었다. The same procedure as in Synthesis Example 27 was carried out except that 2- (3-br omo-5-me t hy 1 pheny 1) -4,6-di henyl-l t 3,5-tr iazine ^-was used. Inv-31 (3.21 g, 50%) was obtained.

GC-Mass (이론치: 603.24 g/mol, 측정치: 603 g/mol)  GC-Mass (Theoretical value: 603.24 g / mol, Measured value: 603 g / mol)

[합성예 32] I 32의 합성  Synthesis Example 32 Synthesis of I 32

Figure imgf000145_0002
Figure imgf000145_0002

3-bromobi phenyl 대신 Instead of 3-bromobi phenyl

2-( 5-bromob i pheny 1 -3-y 1 )-4, 6~d i pheny 1ᅳ 1 , 3 , 5ᅳ t r i az i ne을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-32 (3.47 g, 49 «를 얻었다. 2- (5-bromob i pheny 1 -3-y 1) -4, 6 ~ di pheny 1 ᅳ 1, 3, 5 ᅳ tri az i ne Exc-32 (3.47 g, 49 «) was obtained by the same procedure as in Synthesis Example 27, except for being obtained.

GC-Mass (이론치 : 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 33] Inv~33의 합성  Synthesis Example 33 Synthesis of Inv ~ 33

Figure imgf000146_0001
Figure imgf000146_0001

2， 4-di (bi phenyl -3-yl )-6-(3-chlorophenyl )-l,3,5-triazi ne을 사용하는 것올 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-33 (5.38 g,76 %)를 얻었다.  2, 4-di (bi phenyl-3-yl) -6- (3-chlorophenyl) -l, 3,5-triazi ne except that using the same procedure as in Synthesis Example 29 was the target compound Inv-33 (5.38 g, 76%) was obtained.

Figure imgf000146_0002
Figure imgf000146_0002

2- ( 3-ch 1 oropheny 1 )ᅳ 4 , 6一 d i pheny 1-1,3,5-triazine 대신 2-(3-chlorophenyl)-4,6ᅳ diphenylpyrimidine을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-34 ('4.63 g, 74 «를 얻었다. Synthesis Example except that 2- (3-chlorophenyl) -4,6'diphenylpyrimidine was used instead of 2- (3-ch 1 oropheny 1) ᅳ 4, 6 一 di pheny 1-1,3,5-triazine 29. Inv-34 ( ' 4.63 g, 74 « Got it.

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[합성예 35] Inv-35의 합성  Synthesis Example 35 Synthesis of Inv-35

Figure imgf000147_0001
Figure imgf000147_0001

2- ( 3-ch 1 or opheny 1 )-4 , 6-d i pheny 1 -1 , 3 , 5-t r i az i ne - 대신 Instead of 2- (3-ch 1 or opheny 1) -4, 6-d i pheny 1 -1, 3, 5-t r i az i ne-

2-(3-chloro-5-(tr i f luoromethyl ) phenyl )—4,6—diphenyl—l,3,5—triazine을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-35Except for using 2- (3-chloro-5- (tr if luoromethyl) phenyl) —4,6—diphenyl—l, 3,5—triazine, the same procedure as in Synthesis Example 29 was performed. I nv -35

(4.89 g, 70 %)를 얻었다. (4.89 g, 70%) was obtained.

GC-Mass (이론치: 657.21 g/mol, 측정치: 657 g/mol)  GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

[합성예 36] I r"36의 합성  Synthesis Example 36 Synthesis of I r "36

Figure imgf000147_0002
Figure imgf000147_0002

3一 br omob i pheny 1 대신 4-( 5-bromob i pheny 1ᅳ 3ᅳ y 1 )-2, 6ᅳ d i pheny 1 pyr i m i d i ne을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-36 (3.53 g, 50 를 얻었다. GC-Mass (이론치: 664.26 g/mol, 측정치: 664 g/mol) The same procedure as in Synthesis Example 27 was performed except that 4- (5-bromob i pheny 1 ᅳ 3 ᅳ y 1) -2, 6 ᅳ di pheny 1 pyr imidi ne was used instead of 3 一 br omob i pheny 1. Inv-36 (3.53 g, 50) was obtained as the target compound. GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

[합성예 37] Inv-37의 합성  Synthesis Example 37 Synthesis of Inv-37

Figure imgf000148_0001
Figure imgf000148_0001

3-bromobi phenyl 대신 3-bromo-9-(4, 6-d i phenyl -1 ,3,5-triazi η-2-y 1 )-9H-carbazo 1 e을 사용하 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-37 (3.39 g, 47 %)를 얻었다.  Synthesis Example 27 except that 3-bromo-9- (4, 6-diphenylphenyl-1,3,5-triazi η-2-y 1) -9H-carbazo 1 e was used instead of 3-bromobi phenyl. Inv-37 (3.39 g, 47%) as a target compound was obtained.

GC-Mass (이론치: 678.25 g/mol, 측정치: 678 g/mol)  GC-Mass (Theoretical value: 678.25 g / mol, Measured value: 678 g / mol)

[합성예 38] Inv-38의 합성  Synthesis Example 38 Synthesis of Inv-38

Figure imgf000148_0002
Figure imgf000148_0002

3-bromobi phenyl 대신 (4—bromophenyl )diphenylborane을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-38 (2.44 g, 44 %)를 얻었다. Inv-38 (2.44 g, 44%) was obtained by the same procedure as in Synthesis Example 27, except that (4—bromophenyl) diphenylborane was used instead of 3-bromobi phenyl.

GC-Mass (이론치: 522.23 g/mol, 측정치: 522 g/mol)  GC-Mass (Theoretical value: 522.23 g / mol, Measured value: 522 g / mol)

[합성예 39] Inv-39의 합성

Figure imgf000149_0001
Synthesis Example 39 Synthesis of Inv-39
Figure imgf000149_0001

3-bromobi phenyl 대신 ( 4-br omopheny 1 ) d i heny 1 phosph i ne^: 사용하는 것올 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-39 (2.59 g, 45 %)를 얻었다. Inv-39 (2.59 g , 45%) was prepared in the same manner as in Synthesis Example 27, except that (4-br omopheny 1) di heny 1 phosphine was used instead of 3-bromobi phenyl. Got it.

GC-Mass (이론치: 542.19 g/mol, 측정치: 542 g/mol)  GC-Mass (Theoretical value: 542.19 g / mol, Measured value: 542 g / mol)

[합성예 40] Invᅳ 40의 합성  Synthesis Example 40 Synthesis of Inv'40

Figure imgf000149_0002
Figure imgf000149_0002

2-(3-ch 1 oropheny l)-4, 6-d i pheny 1-1,3,5-tr iazine 대신 2- (3-ch 1 oropheny l) -4, 6-d i pheny 1-1,3,5-tr iazine

(4-chlorophenyl)triphenylsilane을 사용하는 것을 제외하고는 상기 합성예 29과 동일한과정올 수행하여 목적 화합물인 lnv-40 (4.92 g, 75 «를 얻었다. Except for using (4-chlorophenyl) triphenylsilane was carried out in the same manner as in Synthesis Example 29 to obtain the target compound lnv-40 (4.92 g, 75 «.

GC-Mass (이론치: 616.23 g/mol, 측정치: 616 g/mol)  GC-Mass (Theoretical value: 616.23 g / mol, Measured value: 616 g / mol)

[합성예 41] Inv~41의 합성  Synthesis Example 41 Synthesis of Inv ~ 41

Figure imgf000149_0003
IC-lb대신 IC— la를 사용하는 것올 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-41 (4.51 g, 72 ¾>)를 얻었다.
Figure imgf000149_0003
Except for using IC-la instead of IC-lb was carried out the same procedure as in Synthesis Example 29 to obtain the target compound Inv-41 (4.51 g, 72 ¾>).

GC-Mass (이론치 : 589.23 g/mol, 측정치 : 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 42] Inv-42의 합성  Synthesis Example 42 Synthesis of Inv-42

Figure imgf000150_0001
Figure imgf000150_0001

IC-lb 대신 IC-10a를 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정올수행하여 목적 화합물인 Inv-42 (2.35 g, 51 %)를 얻었다.  Except for using IC-10a instead of IC-lb was carried out in the same manner as in Synthesis Example 27 to obtain the target compound Inv-42 (2.35 g, 51%).

GC-Mass (이론치 : 434.18 g/mol , 측정치: 434 g/mol)  GC-Mass (Theoretical value: 434.18 g / mol, Measured value: 434 g / mol)

[합성예 43] Inv-43의 합성  Synthesis Example 43 Synthesis of Inv-43

Figure imgf000150_0002
Figure imgf000150_0002

ICᅳ lb와 3ᅳ bromobiphenyl대신 IC_10a와 3ᅳ (4一 bromophenyl)pyridine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-43 (2.45 g, 53 ¾)를 얻었다.  Inv-43 (2.45 g, 53 ¾) was obtained in the same manner as in Synthesis Example 27, except that IC_10a and 3 ᅳ (4 一 bromophenyl) pyridine were used instead of IC ᅳ lb and 3 ᅳ bromobiphenyl. .

GC-Mass (이론치: 435.17 g/mol, 측정치: 435 g/mol)  GC-Mass (Theoretical value: 435.17 g / mol, Measured value: 435 g / mol)

[합성예 44] I r44의 합성 Synthesis Example 44 Synthesis of I r44

Figure imgf000151_0001
Figure imgf000151_0001

IC-lb 대신 IC-lOa을 사용하는 것을 제외하고는 상기 합성예 29와 동일한과정을 수행하여 목적 화합물인 Inv-44 (4.32 g, 69 W를 얻었다.  Exc-44 (4.32 g, 69 W) was obtained in the same manner as in Synthesis Example 29, except that IC-lOa was used instead of IC-lb.

GC-Mass (이론치: 589.23 g/mol, 측정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 45] Inv-45의 합성  Synthesis Example 45 Synthesis of Inv-45

Figure imgf000151_0002
Figure imgf000151_0002

IOlb와 2-(3-chlorophenyl)-4,6-diphenyl-l,3,5-triazine 대신 IC-lOa 와 2-(3-chlorophenyl)— 4,6-di(pyridin-2-yl)-l,3,5-triazine을 사용하는 것을 제외하고는 상기 합성예 29와 동일한 과정을 수행하여 목적 화합물인 Inv-45 (4.53 g, 72 %)를 얻었다.  IC-lOa and 2- (3-chlorophenyl) — 4,6-di (pyridin-2-yl) -l instead of IOlb and 2- (3-chlorophenyl) -4,6-diphenyl-l, 3,5-triazine Except for using 3,5-triazine was carried out in the same manner as in Synthesis Example 29 to obtain the target compound Inv-45 (4.53 g, 72%).

GC-Mass (이론치: 591.22 g/mol, 측정치: 591 g/mol)  GC-Mass (Theoretical value: 591.22 g / mol, Measured value: 591 g / mol)

[합성예 46] Inv-46의 합성 Synthesis Example 46 Synthesis of Inv-46

Figure imgf000152_0001
Figure imgf000152_0001

IC-lb와 3-bromobi phenyl 대신 IC-lOa와 With IC-lOa instead of IC-lb and 3-bromobi phenyl

2-(3-br omo-5-met hy 1 pheny 1 ) _4， 6—d i pheny 1ᅳ 1,3,5—triazine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-46 (2.95 g, 46 %)를 얻었다. Except for using 2- (3-br omo-5-met hy 1 pheny 1) _4 ， 6—di pheny 1 ᅳ 1,3,5—triazine, the same procedure as in Synthesis Example 27 was performed. Phosphorus Inv-46 (2.95 g, 46%) was obtained.

GC-Mass (이론치 : 603.24 g/mol , 측정치 : 603 g/mol)  GC-Mass (Theoretical value: 603.24 g / mol, Measured value: 603 g / mol)

[합성예 47] Inv-47의 합성  Synthesis Example 47 Synthesis of Inv-47

Figure imgf000152_0002
Figure imgf000152_0002

IC-lb와 3-bromobi phenyl 대신 IC-lOa와 With IC-lOa instead of IC-lb and 3-bromobi phenyl

2— (5—bromobiphenyl—3—yl)—4,6—diphenyl— 1,3,5—triazine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-47 (3.18 g, 45 «를 얻었다. Except for using 2— (5—bromobiphenyl—3—yl) —4,6—diphenyl— 1,3,5—triazine, the same procedure as in Synthesis Example 27 was carried out to obtain Inv-47 (3.18). g, 45 «was obtained.

GC-Mass (이론치 : 665.26 g/mol , 측정치 : 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 48] Inv-48의 합성

Figure imgf000153_0001
Synthesis Example 48 Synthesis of Inv-48
Figure imgf000153_0001

I O lb와 2-(3-chl oropheny 1 ) -4， 6— d i pheny卜 1， 3， 5- 1 r i az i ne 대신  I O lb and 2- (3-chl oropheny 1) -4 ， 6— d i pheny 卜 1 ， 3 ， 5- 1 r i az i ne instead

IC-lOa와 2,4-di(bipheny卜 3— yl)-6-(3-chlorophenyl)-l,3,5— triazine을 사용하 것을 제외하고는 상기 합성예 29와 동일한 과정을 수행하여 목적 화합물인 (6.07 g, 77 %)를 얻었다.  The same procedure as in Synthesis Example 29 was carried out except that IC-lOa and 2,4-di (bipheny 卜 3—yl) -6- (3-chlorophenyl) -1,3,5 triazine were used. Obtained (6.07 g, 77%) as a compound.

GC-Mass (이론치: 741.29 g/mol, 측정치 : 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 49] Inv^49의 합성  Synthesis Example 49 Synthesis of Inv ^ 49

Figure imgf000153_0002
Figure imgf000153_0002

IOlb와 2-(3-chlorophenyl )-4 , 6-di heny 1-1 ,3,5-triazine 대신 IOlb and 2- (3-chlorophenyl) -4, instead of 6-di heny 1-1, 3,5-triazine

IOlOa와 2-(3-chlorophenyl)-4,6-diphenylpyrimidine을 사용하는 것을 제외하고 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 lnv-49 (4.69 g, 75 를 얻었다.  A target compound lnv-49 (4.69 g, 75) was obtained in the same manner as in Synthesis Example 29, except that IOlOa and 2- (3-chlorophenyl) -4,6-diphenylpyrimidine were used.

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol) [합성예 50] Inv~50의 합성 GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol) Synthesis Example 50 Synthesis of Inv ~ 50

Figure imgf000154_0001
Figure imgf000154_0001

IOlb와 2-(3-chlorophenyl)-4,6-diphenyl-l,3,5-triazine 대신  IOlb and 2- (3-chlorophenyl) -4,6-diphenyl-l, 3,5-triazine instead

IC-lOa와 2-(3-chlorophenyl)-4,6-di(pyridin-2-yl)pyrimidine을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정올 수행하여 목적 화합물인 lnv-50 (4.46 g, 71 «를 얻었다. Except for using IC-lOa and 2- (3-chlorophenyl) -4,6-di (pyridin-2-yl) pyrimidine, the same procedure as in Synthesis Example 29 was carried out to obtain lnv-50 (4.46) as a target compound. g, 71 «was obtained.

GC-Mass (이론치: 590.22 g/mol, 측정치: 590 g/mol)  GC-Mass (Theoretical value: 590.22 g / mol, Measured value: 590 g / mol)

[합성예 51] Inv~51의 합성  Synthesis Example 51 Synthesis of Inv ~ 51

Figure imgf000154_0002
Figure imgf000154_0002

IOlb와 3-bromobi henyl 대신 10a와 With 10a instead of IOlb and 3-bromobi henyl

4-(5-br omobi pheny l-3-yl) -2, 6-di phenyl pyr imidi ne을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-51 (3.04 g, 43 를 얻었다. Inv-51 (3.04 g) was prepared by the same procedure as in Synthesis Example 27, except that 4- (5-br omobi pheny l-3-yl) -2 and 6-di phenyl pyr imidi ne were used. , 43 was obtained.

GC-Mass (이론치: 664.26 g/mol, 측정치: 664 g/mol) [합성예 52] Inv-52의 합성 GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol) Synthesis Example 52 Synthesis of Inv-52

Figure imgf000155_0001
Figure imgf000155_0001

IOlb와 3-bromobi henyl 대신 IC-lOa와  With IC-lOa instead of IOlb and 3-bromobi henyl

3-bromo-9-(4, 6-d i phenyl -1 ,3,5-tri azin-2-yl )-9H-carbazole을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv— 52 (2.96 g, 41 «를 얻었다.  Except for using 3-bromo-9- (4, 6-di phenyl -1,3,5-tri azin-2-yl) -9H-carbazole, the same procedure as in Synthesis Example 27 was conducted. Phosphorus Inv— 52 (2.96 g, 41 «was obtained.

GC-Mass (이론치: 678.25 g/mol, 측정치: 678 g/mol)  GC-Mass (Theoretical value: 678.25 g / mol, Measured value: 678 g / mol)

[합성예 53] Inv-53의 합성  Synthesis Example 53 Synthesis of Inv-53

Figure imgf000155_0002
Figure imgf000155_0002

IOlb와 3-bromobi phenyl 대신 IC-10a와 (4-bromophenyl ) diphenylborane을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-53 (2.66 g, 48 를 얻었다. Except for using IC-10a and (4-bromophenyl) diphenylborane instead of IOlb and 3-bromobi phenyl was carried out in the same manner as in Synthesis Example 27 to obtain the target compound I nv -53 (2.66 g, 48).

GC-Mass (이론치: 522.23 g/raol, 측정치： 522 g/mol)  GC-Mass (Theoretical value: 522.23 g / raol, Measured value: 522 g / mol)

[합성예 54] Ιη\τ·54의 합성

Figure imgf000156_0001
Synthesis Example 54 Synthesis of Ιη \ τ · 54
Figure imgf000156_0001

IC一 lb와 3-bromobi henyl 대신 IOlOa와 (4-bromophenyl ) di phenyl phosphine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-54 (2.54 g, 44 를 얻었다. Inv-54 (2.54 g, 44) was obtained in the same manner as in Synthesis Example 27, except that IOlOa and (4-bromophenyl) diphenyl phosphine were used instead of IClb and 3-bromobi henyl.

GC-Mass (이론치: 542.19 g/mol, 측정치 : 542· g/mol)  GC-Mass (Theoretical value: 542.19 g / mol, Measured value: 542 · g / mol)

[합성예 55] Im 55의 합성  Synthesis Example 55 Synthesis of Im 55

Figure imgf000156_0002
Figure imgf000156_0002

Toluene nv- Toluene nv-

I C一 lb와 2-( 3-ch 1 oropheny 1 )-4, 6ᅳ d i heny 1-1,3,5-triazine 대신 I C I lb and 2- (3-ch 1 oropheny 1) -4, 6 ᅳ d i heny 1-1,3,5-triazine instead

IC-lOa와 (4— chlorophenyOtriphenylsilane을 사용하는 것을 제외하고는 상기 합성예 29와 동일한 과정을 수행하여 목적 화합물인 lnv-55 (4.65 g, 71 %)를 얻었다.  Except for using IC-lOa and (4-chlorophenyOtriphenylsilane) was carried out in the same manner as in Synthesis Example 29 to obtain the target compound lnv-55 (4.65 g, 71%).

GC-Mass (이론치: 616.23 g/mol, 측정치: 616 g/mol)  GC-Mass (Theoretical value: 616.23 g / mol, Measured value: 616 g / mol)

[합성예 56] Inv-56의 합성

Figure imgf000157_0001
Synthesis Example 56 Synthesis of Inv-56
Figure imgf000157_0001

IC-lb대신 IC-lOb를 사용하는 것을 제외하고는 상기 합성예 29와 동일한 과정을 수행하여 목적 화합물인 lnv-56 (4.70 g, 75 %)를 얻었다.  Except for using IC-lOb instead of IC-lb was carried out the same procedure as in Synthesis Example 29 to obtain the target compound lnv-56 (4.70 g, 75%).

GC-Mass (이론치 : 589.23 g/mol , 측정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 57] Inv-57의 합성  Synthesis Example 57 Synthesis of Inv-57

Figure imgf000157_0002
Figure imgf000157_0002

IC-lb대신 IC-2를 사용하는 것을 제외하고는 상기 합성예 29와 동일한 과정을수행하여 목적 화합물인 Inv-57 (4.57 g, 73 %)를 얻었다. Exc-57 (4.57 g, 73%) was obtained by the same procedure as in Synthesis Example 29, except that IC-2 was used instead of IC-lb.

GC-Mass (이론치: 589.23 g/mol, 측정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 58] Inv-58의 합성  Synthesis Example 58 Synthesis of Inv-58

Figure imgf000157_0003
IC-lb대신 IC-3을 사용하는 것을 제외하고는 상기 합성예 29와 동일한 과정을수행하여 목적 화합물인 Inv-58 (4.82 g' 77 %)를 얻었다.
Figure imgf000157_0003
Exc-58 (4.82 g '77%) was obtained by the same procedure as in Synthesis Example 29, except that IC-3 was used instead of IC-lb.

GC-Mass (이론치 : 589.23 g/mol, 축정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Accumulated value: 589 g / mol)

[합성예 59] ΙΠ 59의 합성  Synthesis Example 59 Synthesis of ΙΠ 59

Figure imgf000158_0001
Figure imgf000158_0001

질소 기류 하에서 IC-6b(5g, 13.84 mmol)과' phenylboronic acid (2.03 g, 16.61 mmol), NaOH (1.66g, 41.52 mmol)및 THF7H20(100 ml/500 ml )를 흔합한 다음， 40°C에서 Pd(PPh3)4(0.80 g, 5 moI«를 넣고 80°C에서 12시간동안 교반하였다. Under a stream of nitrogen, IC-6b (5 g, 13.84 mmol) and ' phenylboronic acid (2.03 g, 16.61 mmol), NaOH (1.66 g, 41.52 mmol) and THF7H 2 0 (100 ml / 500 ml) were mixed and then 40 ° Pd (PPh 3 ) 4 (0.80 g, 5 moI «in C was added thereto and stirred at 80 ° C. for 12 hours.

반웅 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:EA = 3:1 (v/v))로 정제하여 3,7-diphenyl-3,l()-dihydropyrrolo[3,2-a]carbazoIe을 얻었으며， 얻어진 화합물은 IC-lb 대신 사용하여 상기 합성예 29와 동일한 과정을 수행하여 목적 화합물인 Inv-59 (6.27 g, 68 %)를 얻었다. After completion of reaction, the mixture was extracted with methylene chloride and MgS0 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 3,7-diphenyl-3, l ()-dihydropyrrolo [3,2-a] carbazoIe. In addition, the obtained compound was used in place of IC-lb to carry out the same procedure as in Synthesis Example 29 to obtain Inv-59 (6.27 g, 68%) as a target compound.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 60] Inv~60의 합성  Synthesis Example 60 Synthesis of Inv ~ 60

Figure imgf000158_0002
phenylboronic acid대신 9-pheny 1 ~9H-car bazo 1 -3-y 1 bor on i c acid을사용하는 것을 제외하고는 상기 합성예 59와 동일한 과정을 수행하여 목적 화합물인 Inv-60 (7.94 g, 69 %)를 얻었다.
Figure imgf000158_0002
Inv-60 (7.94 g, 69) was prepared in the same manner as in Synthesis Example 59, except that 9-pheny 1 to 9H-car bazo 1-3-y 1 bor on ic acid was used instead of phenylboronic acid. %) Was obtained.

GC-Mass (이론치: 830.32 g/mol, 측정치: 830 g/mol)  GC-Mass (Theoretical value: 830.32 g / mol, Measured value: 830 g / mol)

[합성예 61] Inv-61의 합성  Synthesis Example 61 Synthesis of Inv-61

Figure imgf000159_0001
ouene
Figure imgf000159_0001
ouene

IC-6b 대신 IC-11을 사용하는 것을 제외하고는 상기 합성예 59와 동일한 과정을 수행하여 목적 화합물인 Inv-61 (6.64 g, 72 ¾)를 얻었다.  Exc-61 (6.64 g, 72 3/4) was obtained by the same procedure as in Synthesis Example 59, except that IC-11 was used instead of IC-6b.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 62] Inv-62의 합성  Synthesis Example 62 Synthesis of Inv-62

Figure imgf000159_0002
Figure imgf000159_0002

IC-6b와 phenylboronic acid 대신 IC-11과 IC-11 instead of IC-6b and phenylboronic acid

9- ( 4 , 6-d i pheny 1 pyr i d i n~2-y 1 ) -9H~car bazo 1 -3-y 1 bor on i c acid을 사용하는 것을 제외하고는 상기 합성예 59와동일한 과정을 수행하여 목적 화합물인 Inv-62 (10.22 g, 75 %)를 얻었다. . Except for using 9- (4, 6-di pheny 1 pyr idin ~ 2-y 1) -9H ~ car bazo 1 -3-y 1 bor on ic acid Inv-62 (10.22) g, 75%). .

GC-Mass (이론치 : 983.37 g/mol, 측정치: 983 g/mol)  GC-Mass (Theoretical value: 983.37 g / mol, Measured value: 983 g / mol)

[합성예 63] Inv-63의 합성  Synthesis Example 63 Synthesis of Inv-63

Figure imgf000160_0001
Figure imgf000160_0001

IC-lb 대신 IC-12를 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정올 수행하여 목적 화합물인 Invᅳ 63 (4.34 g, 71 %)를 얻었다.  Exc. 63 (4.34 g, 71%) was obtained by the same procedure as in Synthesis Example 29, except that IC-12 was used instead of IC-lb.

GC-Mass (이론치 : 603.24 g/mol , 측정치 : 603 g/mol)  GC-Mass (Theoretical value: 603.24 g / mol, Measured value: 603 g / mol)

[합성예 64] Inv-64의 합성  Synthesis Example 64 Synthesis of Inv-64

Figure imgf000160_0002
Figure imgf000160_0002

IC-lb와 3-bromobiphenyl 대신 KXL2와 With KXL2 instead of IC-lb and 3-bromobiphenyl

2- ( 5-br omob i pheny 1 -3-y 1 ) -4 , 6-d i pheny 1-1, 3, 5-triazi ne¾- 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-64 (3.58 g, 52 %)를 얻었다. GC-Mass (이론치 : 679.27 g/mol, 측정치 : 679 g/mol) The same procedure as in Synthesis Example 27 was carried out except that 2- (5-br omob i pheny 1 -3-y 1) -4, 6-di pheny 1-1, 3, 5-triazi ne¾- was used. Inv-64 (3.58 g, 52%) was obtained as the target compound. GC-Mass (Theoretical value: 679.27 g / mol, Measured value: 679 g / mol)

[합성예 65] Inv-65의 합성  Synthesis Example 65 Synthesis of Inv-65

Figure imgf000161_0001
Figure imgf000161_0001

IOlb와 2-(3-chlorophenyl)-4,6-diphenyl-l,3,5-triazine 대신 IC-12와 2,4-di(bi pheny 1— 3-y 1 ) -6- ( 3-ch 1 or opheny 1 ) -1， 3， 5- 1 r i az i ne을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-65 (5.20 gᅳ 68 %)를 얻었다.  IC-12 and 2,4-di (bi pheny 1— 3-y 1) -6- (3-ch instead of IOlb and 2- (3-chlorophenyl) -4,6-diphenyl-l, 3,5-triazine 1 or opheny 1) -1, 3, 5- 1 Ri az i ne was carried out in the same manner as in Synthesis Example 29 to obtain the target compound Inv-65 (5.20 g ᅳ 68%).

GC-Mass (이론치: 775.30 g/mol, 측정치: 775 g/mol)  GC-Mass (Theoretical value: 775.30 g / mol, Measured value: 775 g / mol)

[합성예 66] Inv-66의 합성  Synthesis Example 66 Synthesis of Inv-66

Figure imgf000161_0002
Figure imgf000161_0002

IC-lb 대신 IC-13을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을수행하여 목적 화합물인 Inv-66 (3.90 g, 70 %)를 얻었다.  Exc-66 (3.90 g, 70%) was obtained by the same procedure as in Synthesis Example 29, except that IC-13 was used instead of IC-lb.

GC-Mass (이론치 : 665.26 g/mol , 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 67] Inv-67의 합성 I

Figure imgf000162_0001
Synthesis Example 67 Synthesis of Inv-67 I
Figure imgf000162_0001

2-(4-bromophenyl)-4,6-diphenylpyrimidine을 사용하는 것을 제외하고는 상기 합성예 3과 동일한과정을 수행하여 목적 화합물인 Inv-67 (2.67 g, 48 %)를 얻었다.  Except for using 2- (4-bromophenyl) -4,6-diphenylpyrimidine was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Inv-67 (2.67 g, 48%).

GC-Mass (이론치 : 664.26 g/mol , 측정치: 664 g/mol)  GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

[합성예 68] Imr~68의 합성  Synthesis Example 68 Synthesis of Imr-68

Figure imgf000162_0002
Figure imgf000162_0002

IC-lb 대신 IC-14을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-68 (3.74 g, 73 %)를 얻었다.  Exc-68 (3.74 g, 73%) was obtained by the same procedure as in Synthesis Example 29, except that IC-14 was used instead of IC-lb.

GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 69] Inv69의 합성 Synthesis Example 69 Synthesis of Inv69

Figure imgf000163_0001
Figure imgf000163_0001

IC-lb와 3-bromobi phenyl 대신 I014과 IC014 and I014 instead of 3-bromobi phenyl

2-(5-bromobiphenyl-3— yl)-4,6-diphenyl-l,3,5— triazine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-69 (2.94 g, 52 %)를 얻었다. Except for using 2- (5-bromobiphenyl-3—yl) -4,6-diphenyl-l, 3,5 triazine, the same procedure as in Synthesis Example 27 was carried out to obtain Inv-69 (2.94) as a target compound. g, 52%).

GC-Mass (이론치 : 817.32 g/mol, 측정치 : 817 g/mol)  GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

[합성예 70] Inv-70의 합성  Synthesis Example 70 Synthesis of Inv-70

Figure imgf000163_0002
Figure imgf000163_0002

IC-lb와 3-bromobi phenyl 대신 IC-14과 IC-14 instead of IC-lb and 3-bromobi phenyl

3,3'-(5-3 皿)-1,3-1)11^ 1^6)^ ^(1^6을 사용하는 것을 제외하고는 상기 합성예 27과동일한 과정을 수행하여 목적 화합물인 Inv-70 (2.34 g, 51 %)를 얻었다. 3,3 '-(5-3 皿) -1,3-1) 11 ^ 1 ^ 6) ^ ^ (1 ^ 6 was carried out in the same manner as in Synthesis Example 27 except that the target compound Inv-70 (2.34 g, 51%) was obtained.

GC-Mass (이론치: 664.26 g/mol, 측정치: 664 g/mol)  GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

[합성예 71] Inv-기의 합성

Figure imgf000164_0001
Synthesis Example 71 Synthesis of Inv-Group
Figure imgf000164_0001

IC-lb와 3-bromobi henyl 대신 IC-14와 With IC-14 instead of IC-lb and 3-bromobi henyl

3-bromo-9-(4, 6-d i pheny 1-1 ,3,5-triazi η-2-yl )-9H-carbazo 1 e을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정올 수행하여 목적 화합물인 Inv-71 (2.81 g, 49 %)를 얻었다. The same procedure as in Synthesis Example 27 was conducted except that 3-bromo-9- (4, 6-dipheny 1-1,3,5-triazi η-2-yl) -9H-carbazo 1 e was used. Inv-71 (2.81 g, 49%) was obtained.

GC-Mass (이론치 : 830.32 g/mol , 측정치: 830 g/mol)  GC-Mass (Theoretical value: 830.32 g / mol, Measured value: 830 g / mol)

[합성예 72] Inv-72의 합성  Synthesis Example 72 Synthesis of Inv-72

Figure imgf000164_0002
Figure imgf000164_0002

IC-lb 대신 IC-15를 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을수행하여 목적 화합물인 Inv-72 (4.05 g, 72 %)를 얻었다.  Exc-72 (4.05 g, 72%) was obtained by the same procedure as in Synthesis Example 29, except that IC-15 was used instead of IC-lb.

GC-Mass (이론치: 657.21 g/mol, 측정치: 657 g/mol)  GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

[합성예 73] Inv-73의 합성

Figure imgf000165_0001
Synthesis Example 73 Synthesis of Inv-73
Figure imgf000165_0001

IC-lb와 2-(3-chlorophenyl)-4,6-dipheny卜 1,3,5-triazine 대신 IC-15와 3-bromo-9-(4， 6-di phenyl -1 ,3,5-triazi n_2-y 1 )-9H-carbazo le을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-73 (3.66 g, 65 %)를 얻었다.  IC-lb and 2- (3-chlorophenyl) -4,6-dipheny 卜 instead of 1,3,5-triazine IC-15 and 3-bromo-9- (4, 6-diphenyl-1,3,5- Inv-73 (3.66 g, 65%) was obtained by the same procedure as in Synthesis Example 29, except that triazi n_2-y 1) -9H-carbazo le was used.

GC-Mass (이론치: 657.21 g/mol, 측정치: 657 g/mol)  GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

[합성예 74] 1 74의 합성  Synthesis Example 74 Synthesis of 1 74

Figure imgf000165_0002
Figure imgf000165_0002

IC-lb와 3-bromobi phenyl 대신 IC-15와 IC-15 and IC-15 instead of 3-bromobi phenyl

2-(3-bromophenyl)-4,6-diphenylpyrimidine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 hw-74 (2.64 g, 47 %)를 얻었다. Except for using 2- (3-bromophenyl) -4,6-diphenylpyrimidine was carried out the same procedure as in Synthesis Example 27 to obtain the target compound hw-74 (2.64 g, 47%).

GC-Mass (이론치: 656.22 g/mol, 측정치: 656 g/mol) [합성예 75] I 75의 합성 GC-Mass (Theoretical value: 656.22 g / mol, Measured value: 656 g / mol) Synthesis Example 75 Synthesis of I 75

Figure imgf000166_0001
Figure imgf000166_0001

IC-lb 대신 IC-16을 사용하는 것올 제외하고는 상기 합성예 29과 동일한 과정을수행하여 목적 화합물인 Inv-75 (3.90 g, 70 %)를 얻었다.  Exc-75 (3.90 g, 70%) was obtained in the same manner as in Synthesis Example 29, except that IC-16 was used instead of IC-lb.

GC-Mass (이론치 : 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 76] Inv-76의 합성  Synthesis Example 76 Synthesis of Inv-76

Figure imgf000166_0002
Figure imgf000166_0002

IC-lb와 2-(3-chlorophenyl)-4,6-diphenyl— 1,3,5-triazine 대신 IC-16과 IC-lb and 2- (3-chlorophenyl) -4,6-diphenyl—IC-16 instead of 1,3,5-triazine

2,4-di(biphenyl-3-yl)-6— (3-chlorophenyl)-l,3,5-triazine을 사용하 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv— 76 (5.00 g, 73 를 얻었다. 2,4-di (biphenyl-3-yl) -6— (3-chlorophenyl) -l, 3,5-triazine was carried out in the same manner as in Synthesis Example 29, except that Inv—, the target compound, was used. 76 (5.00 g, 73 were obtained.

GC-Mass (이론치 : 817.32 g/mol , 측정치: 817 g/mol)  GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

[합성예 77] Inv-77의 합성

Figure imgf000167_0001
Synthesis Example 77 Synthesis of Inv-77
Figure imgf000167_0001

lnv-77  lnv-77

IC-lb 대신 IC-17를 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-77 (3.85 g, 69 ¾)를 얻었다. .  Exc-77 (3.85 g, 69 ¾) was obtained in the same manner as in Synthesis Example 29, except that IC-17 was used instead of IC-lb. .

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/raol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / raol)

[합성예 78] I r78의 합성  Synthesis Example 78 Synthesis of I r78

Figure imgf000167_0002
Figure imgf000167_0002

IC-lb와 3-bromobi henyl 대신 IC-18과 IC-18 instead of IC-lb and 3-bromobi henyl

2-(4ᅳ bromophenyl)-4,6-diphenyl-l,3,5-triazine올 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-78 (2.90 g, 52 %)를 얻었다 Inv-78 (2.90 g, 52%) was prepared in the same manner as in Synthesis Example 27, except that 2- (4 ᅳ bromophenyl) -4,6-diphenyl-1,3,5-triazineol was used. Got

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 79] Inv-79의 합성

Figure imgf000168_0001
Synthesis Example 79 Synthesis of Inv-79
Figure imgf000168_0001

IC-lb 대신 IC-18을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-79 (3.85 g, 69 %)를 얻었다.  Exc-79 (3.85 g, 69%) was obtained in the same manner as in Synthesis Example 29, except that IC-18 was used instead of IC-lb.

GC-Mass (이론치 : 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 80] I 80의 합성  Synthesis Example 80 Synthesis of I 80

Figure imgf000168_0002
과
Figure imgf000168_0002
and

2-(4-bromophenyl)-5-phenylpyrimidine을 사용하는 것을 제외하고는 상기 합성예 27과동일한 과정을 수행하여 목적 화합물인 Inv-80 (2.66 g, 54 )를 얻었다. Except for using 2- (4-bromophenyl) -5-phenylpyrimidine was carried out the same procedure as in Synthesis Example 27 to obtain the target compound Inv-80 (2.66 g, 54).

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[합성예 81] 1 81의 합성  Synthesis Example 81 Synthesis of 1 81

Figure imgf000168_0003
IC-lb 대신 IC-19를 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-81 (3.48 g, 68 %)를 얻었다.
Figure imgf000168_0003
Exc-81 (3.48 g, 68%) was obtained by the same procedure as in Synthesis Example 29, except that IC-19 was used instead of IC-lb.

GC-Mass (이론치 : 741.29 g/mol, 측정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 82] Inv-82의 합성  Synthesis Example 82 Synthesis of Inv-82

Figure imgf000169_0001
Figure imgf000169_0001

IC lb와 3-bromobi phenyl 대신 ICᅳ 19와 2- ( 4-br omopheny D yrimidine-i- 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-82 (1.99 g, 49 %)를 얻었다.  The same procedure as in Synthesis Example 27 was carried out except for the use of IC ᅳ 19 and 2- (4-bromopheny D yrimidine-i- in place of IC lb and 3-bromobi phenyl. 49%).

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[할성예 83] Inv-83의 합성  [Active Example 83] Synthesis of Inv-83

Figure imgf000169_0002
Figure imgf000169_0002

IC-lb 대신 IC-20올 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-83 (4.00 g, 71 %)를 얻었다.  Exc-83 (4.00 g, 71%) was obtained in the same manner as in Synthesis Example 29, except that IC-20ol was used instead of IC-lb.

GC-Mass (이론치: 657.21 g/mol, 측정치: 657 g/mol)  GC-Mass (Theoretical value: 657.21 g / mol, Measured value: 657 g / mol)

[합성예 84] Inv-84의 합성

Figure imgf000170_0001
Synthesis Example 84 Synthesis of Inv-84
Figure imgf000170_0001

IOlb와 3-bromobi phenyl 대신 IC-20과 IC-20 instead of IOlb and 3-bromobi phenyl

2-(5-br omob i pheny 1-3-yl )-4, 6-d i pheny 1-1,3,5-tr iazine^: 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-84 (2.89 g, 46 %)를 얻었다. 2- (5-br omob i pheny 1-3-yl) -4, 6-di pheny 1-1,3,5-tr iazine ^: The same procedure as in Synthesis Example 27 was carried out except that Inv-84 (2.89 g, 46%) was obtained as the target compound.

GC-Mass (이론치 : 733.25 g/mol, 측정치: 733 g/mol)  GC-Mass (Theoretical value: 733.25 g / mol, Measured value: 733 g / mol)

[합성예 85] Inv-85의 합성  Synthesis Example 85 Synthesis of Inv-85

Figure imgf000170_0002
Figure imgf000170_0002

IC-lb 대신 IC-21을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을수행하여 목적 화합물인 Inv-85 (3.49 g, 69 %)를 얻었다.  Exc-85 (3.49 g, 69%) was obtained by the same procedure as in Synthesis Example 29, except that IC-21 was used instead of IC-lb.

GC-Mass (이론치 : 754.28 g/mol ' 측정치: 754 g/mol)  GC-Mass (Theoretical value: 754.28 g / mol 'Measured value: 754 g / mol)

[합성예 86] Inv~86의 합성

Figure imgf000171_0001
Synthesis Example 86 Synthesis of Inv ~ 86
Figure imgf000171_0001

IC-lb와 3-bromobi henyl 대신 IC-21과IC-21 instead of IC-lb and 3-bromobi henyl

3-bromo-9— (4,6-diphenyl-l,3,5-triazin-2-yl)-9H-carbazole을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-86 (2.49 g, 44 를 얻었다. 3-bromo-9— (4,6-diphenyl-l, 3,5-triazin-2-yl) -9H-carbazole was followed in the same manner as in Synthesis Example 27 to carry out Inv as the target compound. -86 (2.49 g, 44 was obtained.

GC-Mass (이론치 : 843.31 g/mol, 측정치: 843 g/mol)  GC-Mass (Theoretical value: 843.31 g / mol, Measured value: 843 g / mol)

[합성예 87] Inv-87의 합성  Synthesis Example 87 Synthesis of Inv-87

Figure imgf000171_0002
Figure imgf000171_0002

ICᅳ lb와 3-bromobi phenyl 대신 ICᅳ 22와 Iodobenzene을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-87 (1.62 g, 48 %)를 얻었다.  Exc-87 (1.62 g, 48%) was obtained by the same procedure as in Synthesis Example 27, except that IC ᅳ 22 and Iodobenzene were used instead of IC ᅳ lb and 3-bromobi phenyl.

GC-Mass (이론치: 678.25 g/mol, 측정치: 678 g/mol)  GC-Mass (Theoretical value: 678.25 g / mol, Measured value: 678 g / mol)

[합성예 88] Inv^88의 합성 Synthesis Example 88 Synthesis of Inv ^ 88

Figure imgf000172_0001
Figure imgf000172_0001

IC-lb와 3-bromobi phenyl 대신 IC-22와 1-brom으 3,5_diphenyl benzene올 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-88 (1.94 g, 47 %)를 얻었다.  Inv-88 (1.94 g, 47%) was carried out in the same manner as in Synthesis Example 27, except that 3,5_diphenyl benzene was used as IC-22 and 1-brom instead of IC-lb and 3-bromobi phenyl. )

GC-Mass (이론치: 830.32 g/mol, 측정치: 830 g/mol)  GC-Mass (Theoretical value: 830.32 g / mol, Measured value: 830 g / mol)

[합성예 89] Inv-89의 합성  Synthesis Example 89 Synthesis of Inv-89

Figure imgf000172_0002
Figure imgf000172_0002

IC-lb 대신 IC-23을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-89 (3.79 g, 68 %)를 얻었다.  Exc-89 (3.79 g, 68%) was obtained in the same manner as in Synthesis Example 29, except that IC-23 was used instead of IC-lb.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 90] Inv-90의 합성

Figure imgf000173_0001
Synthesis Example 90 Synthesis of Inv-90
Figure imgf000173_0001

IC-lb 대신 IC-24을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-90 (4.18 g, 75 %)를 얻었다: Exc-90 (4.18 g, 75%) was obtained in the same manner as in Synthesis Example 29, except that IC-24 was used instead of IC-lb:

GC-Mass (이론치: 665.26 g/mol, 측정치: 665.26 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665.26 g / mol)

[합성예 91] Inv-91의 합성  Synthesis Example 91 Synthesis of Inv-91

Figure imgf000173_0002
Figure imgf000173_0002

IC-lb와 2-(3-chlorophenyl)— 4,6-diphenyl-l,3,5-triazine 대신 IC-24과 2 , 4-d i(bi phenyl -3-y 1 )-6-(3-chlorophenyl)-l ,3,5-triazi ne을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-91 (5.07 g, 74 %)를 얻었다.  IC-lb and 2- (3-chlorophenyl) — instead of 4,6-diphenyl-l, 3,5-triazine IC-24 and 2, 4-di (bi phenyl-3-y 1) -6- (3- Inv-91 (5.07 g, 74%) was obtained by the same procedure as in Synthesis Example 29, except that chlorophenyl) -l, 3,5-triazine was used.

GC-Mass (이론치: 817.32 g/mol, 측정치: 817 g/mol)  GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

[합성예 92] Inv-92의 합성

Figure imgf000174_0001
Synthesis Example 92 Synthesis of Inv-92
Figure imgf000174_0001

lnv-92  lnv-92

IC-lb 대신 IC-25를 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv— 92 (4.01 g, 72 %)를 얻었다.  Exc. 92 (4.01 g, 72%) was obtained by the same procedure as in Synthesis Example 29, except that IC-25 was used instead of IC-lb.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 93] Inv^93의 합성  Synthesis Example 93 Synthesis of Inv ^ 93

Figure imgf000174_0002
Figure imgf000174_0002

IC-lb와 3-bromobi phenyl 대신 IC-25와 With IC-25 instead of IC-lb and 3-bromobi phenyl

2-(3-bromophenyl)-4,6-diphenylpyriraidine올 사용하는 것올 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 lnv-93 (2.84 g, 51 «를 얻었다. Except for using 2- (3-bromophenyl) -4,6-diphenylpyriraidineol, the same procedure as in Synthesis Example 27 was carried out to obtain lnv-93 (2.84 g, 51 «) as a target compound.

GC-Mass (이론치 : 664.26 g/mol , 측정치: 664 g/mol)  GC-Mass (Theoretical value: 664.26 g / mol, Measured value: 664 g / mol)

[합성예 94] Inv-94의 합성

Figure imgf000175_0001
Synthesis Example 94 Synthesis of Inv-94
Figure imgf000175_0001

IC-lb 대신 IC-26을 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-94 (3.74 g, 73 «를 얻었다.  Exc-94 (3.74 g, 73 «) was obtained in the same manner as in Synthesis Example 29, except that IC-26 was used instead of IC-lb.

GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 95] Inv"95의 합성  Synthesis Example 95 Synthesis of Inv "95

Figure imgf000175_0002
Figure imgf000175_0002

2一 ( 5—br omob i phenyl -3-yl ) -4 , 6—d i pheny 1— 1， 3 , 5— t r i az i ne을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화할물인 lnv-95 (2.71 g, 48 ¾)를 얻었다.  The same procedure as in Synthesis Example 27 was carried out except that 2 一 (5—br omob i phenyl-3-yl) -4, 6-di pheny 1-1, 3, 5- tri az i ne was used. The desired compound, lnv-95 (2.71 g, 48 ¾), was obtained.

GC-Mass (이론치 : 817.32 g/mol , 측정치 : 817 g/mol)  GC-Mass (Theoretical value: 817.32 g / mol, Measured value: 817 g / mol)

[합성예 96] Inv-96의 합성 Synthesis Example 96 Synthesis of Inv-96

Figure imgf000176_0001
Figure imgf000176_0001

IC-lb와 3-broniobi phenyl 대신 IC-27과 2_(4-bromophenyl)pyridine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv— 96 (2.07 g, 51 «를 얻었다.  Inv— 96 (2.07 g, 51 «) was obtained in the same manner as in Synthesis Example 27, except that IC-27 and 2_ (4-bromophenyl) pyridine were used instead of IC-lb and 3-broniobi phenyl. Got it.

GC-Mass (이론치: 587.24 g/mol, 측정치: 587 g/mol)  GC-Mass (Theoretical value: 587.24 g / mol, Measured value: 587 g / mol)

[합성예 97] Inv-97의 합성  Synthesis Example 97 Synthesis of Inv-97

Figure imgf000176_0002
Figure imgf000176_0002

IC-lb 대신 IC-27를 사용하는 것을 제외하고는 상기 합성예 29과 동일한 과정을 수행하여 목적 화합물인 Inv-97 (4.00 g, 78 W를 얻었다.  Exc-97 (4.00 g, 78 W) was obtained in the same manner as in Synthesis Example 29, except that IC-27 was used instead of IC-lb.

GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 98] Inv-98의 합성 Synthesis Example 98 Synthesis of Inv-98

Figure imgf000177_0001
Figure imgf000177_0001

IC-lb와 3-bromobi phenyl 대신 IC-28과 Iodobenzene을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-98 (1.83 g, 53 «를 얻었다.  Inv-98 (1.83 g, 53 «) was obtained in the same manner as in Synthesis Example 27, except that IC-28 and Iodobenzene were used instead of IC-lb and 3-bromobi phenyl.

GC-Mass (이론치: 589.23 g/mol, 측정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 99] Inv^99의 합성  Synthesis Example 99 Synthesis of Inv ^ 99

Figure imgf000177_0002
Figure imgf000177_0002

IC一 lb와 3-bromobi henyl 대신 ICᅳ 28과 1-br omo-3 , 5-d i phenyl benzene을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-99 (2.25 g, 52 %)를 얻었다.  Inv-99 (2.25) was prepared in the same manner as in Synthesis Example 27, except that IC ᅳ 28, 1-bromo-3, and 5-diphenyl benzene were used instead of IClb and 3-bromobi henyl. g, 52%).

GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 100] Inv-100의 합성 Synthesis Example 100 Synthesis of Inv-100

Figure imgf000178_0001
iC-lb대신 IC-28를 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을수행하여 목적 화합물인 Inv-100 (1.91 g, 49 를 얻었다.
Figure imgf000178_0001
Exc-100 (1.91 g, 49) was obtained by the same procedure as in Synthesis Example 27, except that IC-28 was used instead of iC-lb.

GC-Mass (이론치 : 665.26 g/mol , 측정치 : 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 101] Inv^l()l의 합성  Synthesis Example 101 Synthesis of Inv ^ l () l

Figure imgf000178_0002
Figure imgf000178_0002

IC-lb와 3-bromobi phenyl 대신 IC-29와 Iodobenzene을 사용하는 것을 제외하고는 상기 합성예 27과 동일한과정을수행하여 목적 화합물인 Inv- 101 (1.55 g, 45 %)를 얻었다.  Inv-101 (1.55 g, 45%) was obtained by the same procedure as in Synthesis Example 27, except that IC-29 and Iodobenzene were used instead of IC-lb and 3-bromobi phenyl.

GC-Mass (이론치 : 588.23 g/mol , 측정치 : 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[합성예 102] Inv-102의 합성  Synthesis Example 102 Synthesis of Inv-102

Figure imgf000178_0003
IC-lb와 3-bromobi phenyl 대신 I029와 4-(4ᅳ bromophenyl)pyridine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-102 (1.83 g, 47 %)를 얻었다.
Figure imgf000178_0003
The target compound Inv-102 (1.83 g, 47%) was obtained by the same procedure as in Synthesis Example 27, except that I029 and 4- (4 ᅳ bromophenyl) pyridine were used instead of IC-lb and 3-bromobi phenyl. Got it.

GC-Mass (이론치 : 665.26 g/mol , 측정치 : 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 103] Inv-103의 합성  Synthesis Example 103 Synthesis of Inv-103

Figure imgf000179_0001
Figure imgf000179_0001

IC-lb와 3ᅳ bromobiphenyl 대신 IC— 30과 Iodobenzene을 사용하는 것을 제외하고는 상기 합성예 27과동일한 과정을 수행하여 목적 화합물인 hw— 103 (1.48 g, 43 %)를 얻었다.  Except for using IC-30 and Iodobenzene instead of IC-lb and 3 ᅳ bromobiphenyl was carried out the same procedure as in Synthesis Example 27 to obtain the target compound hw-103 (1.48 g, 43%).

GC-Mass (이론치: 589.23 g/mol, 측정치: 589 g/mol)  GC-Mass (Theoretical value: 589.23 g / mol, Measured value: 589 g / mol)

[합성예 104] I l04의 합성  Synthesis Example 104 Synthesis of I04

Figure imgf000179_0002
Figure imgf000179_0002

IC-lb 대신 IC-30을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정올 수행하여 목적 화합물인 Inv-104 (1.87 g, 48 %)를 얻었다.  Exc-104 (1.87 g, 48%) was obtained in the same manner as in Synthesis Example 27, except that IC-30 was used instead of IC-lb.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol) [합성예 105] Inv-105의 합성 GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol) Synthesis Example 105 Synthesis of Inv-105

Figure imgf000180_0001
Figure imgf000180_0001

IC-lb와 3-bromobi phenyl 대신 IO30과 4-bromobi phenyl을 사용하는 것을 제외하고는 상기 합성예 27과동일한과정올 수행하여 목적 화합물인 Inv-105 (1.75 g, 45 D를 얻었다.  Inv-105 (1.75 g, 45 D) was obtained in the same manner as in Synthesis Example 27, except that IO30 and 4-bromobi phenyl were used instead of IC-lb and 3-bromobi phenyl.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665.26 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665.26 g / mol)

[합성예 106] Inv-106의 합성  Synthesis Example 106 Synthesis of Inv-106

Figure imgf000180_0002
Figure imgf000180_0002

IOlb와 3-bromobi phenyl 대신 IO30과 l-bron -3,5-diphenyl benzene을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-106 (2.12 g, 49 «를 얻었다.  Inv-106 (2.12 g, 49 «) was obtained in the same manner as in Synthesis Example 27, except that IO30 and l-bron-3,5-diphenyl benzene were used instead of IOlb and 3-bromobi phenyl. .

GC-Mass (이론치: 741.29 g/mol, 측정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / mol, Measured value: 741 g / mol)

[합성예 107] Inv-107의 합성 Synthesis Example 107 Synthesis of Inv-107

Figure imgf000181_0001
Figure imgf000181_0001

IC-lb와 3-bromobi phenyl 대신 IC-31과 Iodobenzene을 사용하는 것을 제외하고는 상기 합성예 27과동일한과정을 수행하여 목적 화합물인 lnv-107 (1.79 g, 52 %)를 얻었다.  Except for using IC-31 and Iodobenzene instead of IC-lb and 3-bromobi phenyl was carried out the same procedure as in Synthesis Example 27 to obtain the target compound lnv-107 (1.79 g, 52%).

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[합성예 108] Inv-108의 합성  Synthesis Example 108 Synthesis of Inv-108

Figure imgf000181_0002
Figure imgf000181_0002

ICᅳ lb와 3-bromobi phenyl 대신 IC 31과 1-br omo-3 , 5-d i pheny 1 benzene을 사용하는 것을 제외하고는 상기 합성예 27과 동일한 과정을 수행하여 목적 화합물인 Inv-108 (1.99 g, 46 %)를 얻었다.  Inv-108 (1.99) was prepared in the same manner as in Synthesis Example 27, except that IC 31 and 1-br omo-3 and 5-dipheny 1 benzene were used instead of IC ᅳ lb and 3-bromobi phenyl. g, 46%).

GC-Mass (이론치: 740.29 g/mol, 측정치: 740 g/mol)  GC-Mass (Theoretical value: 740.29 g / mol, Measured value: 740 g / mol)

[합성예 109] Ιην^109의 합성

Figure imgf000182_0001
Synthesis Example 109 Synthesis of Ιην ^ 109
Figure imgf000182_0001

IC-lb와 3-bromobi phenyl 대신 IC-17과 IC-17 instead of IC-lb and 3-bromobi phenyl

2-( 5-bromob i heny 1 -3-y 1 )-4, 6ᅳ d i heny 1ᅳ 1， 3 , 5ᅳ t r i az i ne을 사용하는 것을 제외하고는 상기 합성예 27과동일한 과정을 수행하여 목적 화합물인 Inv-109 (3.54 g, 57 «를 얻었다. Except for using 2- (5-bromob i heny 1-3-y 1) -4, 6 ᅳ di heny 1 ᅳ 1, 3, 5 ᅳ tri az i ne, the same procedure as in Synthesis Example 27 was performed. Inv-109 (3.54 g, 57 «) was obtained as the target compound.

GC-Mass (이론치: 741.29 g/raol' 축정치: 741 g/mol)  GC-Mass (Theoretical value: 741.29 g / raol 'Accumulated value: 741 g / mol)

[합성예 110] In llO의 합성  Synthesis Example 110 Synthesis of In llO

Figure imgf000182_0002
Figure imgf000182_0002

IOlb와 3-bromobi phenyl 대신 IC-23과 IC-23 instead of IOlb and 3-bromobi phenyl

2，2'-(5— bromo-l,3-phenylene)dipyridine을 사용하는 것을 제외하고는 상기 합성예 27과 동일한과정을 수행하여 목적 화합물인 Inv-110 (2.61 g, 53 %)를 얻었다. A target compound Inv-110 (2.61 g, 53%) was obtained in the same manner as in Synthesis Example 27 except for using 2,2 '-(5—bromo-l, 3-phenylene) dipyridine.

GC-Mass (이론치: 588.23 g/mol, 측정치: 588 g/mol)  GC-Mass (Theoretical value: 588.23 g / mol, Measured value: 588 g / mol)

[준비예 32] IC-32a및 IC-32b의 합성 Preparation Example 32 Synthesis of IC-32a and IC-32b

Figure imgf000182_0003
Figure imgf000182_0003

2- ( benzo [b ] t h i ophen~5-y 1 ) -4 , 4 , 5 , 5~t et r amet hy 1 - 1 , 3 , 2-d i oxabor o 1 ane-^l 합성

Figure imgf000183_0001
Synthesis of 2- (benzo [b] thi ophen ~ 5-y 1) -4, 4, 5, 5 ~ t et r amet hy 1-1, 3, 2-di oxabor o 1 ane-^ l
Figure imgf000183_0001

5-br omo-lH- i ndo 1 e 대신 5-br omobenz o [ b ] t h i ophenei 사용하 것을 제외하고 준비예 1의 <단계 1>과 동일한 과정을 수행하여 Except for using 5-br omobenz o [b] t h i ophenei instead of 5-br omo-lH- i ndo 1 e, follow the same procedure as in <Step 1> of Preparation Example 1

2-(benzo[b] thiophen-5-yl)-4， 4， 5， 5-t et r amethy 1 -1， 3， 2-dioxaborol ane을 얻었다. 2- (benzo [b] thiophen-5-yl) -4, 4, 5, 5-t et r amethy 1 -1, 3, 2-dioxaborol ane was obtained.

¾ NMR: δ 1.24 (s, 12H), 7.65 (d, 1H), 7.85 (d, 1H), 7.98 (d, 1H), 8.07 ¾ NMR: δ 1.24 (s, 12H), 7.65 (d, 1H), 7.85 (d, 1H), 7.98 (d, 1H), 8.07

(d, 1H), 8.12 (s, 1H) (d, 1H), 8.12 (s, 1H)

<단계 2> 5-(2-nitrophenyl)benz이; b] thiophene의 합성  <Step 2> 5- (2-nitrophenyl) benz; b] synthesis of thiophene

Figure imgf000183_0002
Figure imgf000183_0002

5-(4,4,5,5-tetramethyl-l,3)2-dioxaborolan-2-yl)-lH-indole 대신 상기 <단계 1>에서 얻은5- (4,4,5,5-tetramethyl-l, 3 ) 2-dioxaborolan-2-yl) -lH-indole obtained in <Step 1> instead of

2- ( benzo [ b ] t h i ophen-5-y 1 )-4,4,5, 5~t et r amethy 1 -1 , 3 , 2-di oxabord 1 ane^r 사용하 것을 제외하고는 준비예 1의 <단계 2〉와 동일한 과정을 수행하여 5- ( 2-n i t r opheny 1 ) benzo [ b ] t h i ophene-§- 얻었다. Preparation example except 2- (benzo [b] thi ophen-5-y 1) -4,4,5, 5 ~ t et r amethy 1 -1, 3, 2-di oxabord 1 ane ^ r The same procedure as in <Step 2> of 1 was carried out to obtain 5- (2-nitr opheny 1) benzo [b] thi ophene-§-.

¾ NMR: δ 7.67 (m, 2H) , 7.88 (m, 2H)， 7.98 (d, 1H)， 8.00 (d, 1H), 8.07 (m, 2H), 8.13 (s, 1H)  ¾ NMR: δ 7.67 (m, 2H), 7.88 (m, 2H), 7.98 (d, 1H), 8.00 (d, 1H), 8.07 (m, 2H), 8.13 (s, 1H)

<단계 3> IC-32a 및 IC-32b의 합성

Figure imgf000184_0001
Step 3 Synthesis of IC-32a and IC-32b
Figure imgf000184_0001

5- ( 2-n i t r opheny 1 ) - 1-pheny 1 - 1H- i ndo 1 e 대신 상기 〈단계 2>에서 얻은 5-(2-nitrophenyl)benzo [b]thiophene을 사용하는 것을 제외하고는 준비예 1의 <단계 4>와 동일한 과정을 수행하여 IC-32a 1.70 g (7.60 mmol, yield ： 35 과 IC-32b 1.89 g (8.46 mmol, yield ： 39%)을 얻었다. Preparation Example except that 5- (2-nitrophenyl) benzo [b] thiophene obtained in the above <Step 2> was used instead of 5- (2-nitr opheny 1)-1-pheny 1-1H-i ndo 1 e 1.70 g (7.60 mmol, yield: 35) and 1.89 g (8.46 mmol, yield: 39%) of IC-32a were obtained by the same procedure as in <Step 4> of 1.

IC-32a의 -丽 R： δ 7.29 (t, IH), 7.59 (m, 3H) , 7.79 (m, 3H) , 8.11 (d, 1H) , 8.26 (s, IH)  IC-32a-li R: δ 7.29 (t, IH), 7.59 (m, 3H), 7.79 (m, 3H), 8.11 (d, 1H), 8.26 (s, IH)

IC-32b의 ¾-NMR： δ 7.29 (t, IH), 7.53 (m, 2H)， 7.81 (m, 3H)， 8.12 (m, 2H), 8.25 (s, IH)  ¾-NMR of IC-32b: δ 7.29 (t, IH), 7.53 (m, 2H), 7.81 (m, 3H), 8.12 (m, 2H), 8.25 (s, IH)

[준비예 33] IC-33의 합성  Preparation 33 Synthesis of IC-33

<단계 1> 4- ( 2- i sopr opy 1 pheny 1 ) -IH- i ndo 1 e 의 합성  <Step 1> Synthesis of 4- (2- i sopr opy 1 pheny 1) -IH- i ndo 1 e

Figure imgf000184_0002
Figure imgf000184_0002

'5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole 대신 4-(4,4,5,5-tetramethyl— l,3,2-dioxaborolan-2-yl)-lH-indole을 사용하고 1-br omo-2-η i t robenzene 대신 l—br이 no— 2— isopropylbenzene을 사용하는 것을 제외하고 준비예 1의 <단계 1>과 동일한 과정을 수행하여 ' 5- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indole instead of 4- (4,4,5,5-tetramethyl— l, 3,2- Use of dioxaborolan-2-yl) -lH-indole and l—br no— 2— isopropylbenzene instead of 1-br omo-2-η it robenzene Except for <Step 1> of Preparation Example 1,

4- ( 2- i sopropy 1 pheny 1 ) - 1H- i ndo 1 e을 얻었다. 4- (2-i sopropy 1 pheny 1) -1H-i ndo 1 e was obtained.

讓 R: δ 1.21 (s, 6Η), 2.87 (m, 1H)， 6.43 (d, 1H), 7.26 (t, 1H) , 7.35 (m, 3H), 7.48 (d, 1H), 7.74 (m, 2H), 7.85 (d, 1H), 8.23 (s, 1H)  讓 R: δ 1.21 (s, 6Η), 2.87 (m, 1H), 6.43 (d, 1H), 7.26 (t, 1H), 7.35 (m, 3H), 7.48 (d, 1H), 7.74 (m, 2H), 7.85 (d, 1H), 8.23 (s, 1H)

<단계 2> IC-33의 합성

Figure imgf000185_0001
<Step 2> Synthesis of IC-33
Figure imgf000185_0001

질소 기류 하에서 상기 <단계 1>에서  In <Step 1> under a stream of nitrogen

4- ( 2- i s opr opy 1 pheny 1 ) - 1H- i ndo 1 e ( 5 g, 21.25 隱 ol)과 RhCl (PPh3)3(98.3 mg, 0.5 mol%)를 1,4— dioxane 50 ml에 녹인 다음 135°C에서 1시간동안교반하였다. 4- (2- is opr opy 1 pheny 1)-1H- i ndo 1 e (5 g, 21.25 隱 ol) and RhCl (PPh 3 ) 3 (98.3 mg, 0.5 mol%) 1,4— dioxane 50 ml It was dissolved in and stirred at 135 ° C for 1 hour.

반응 종결 후 용매를 제거하고 컬럼크로마토그래피 (Hexane:MC = 3:1 After completion of the reaction the solvent was removed and column chromatography (Hexane: MC = 3: 1

(v:v))로 정제하여 IC-33 (4 g, 수율 81%)을 얻었다. (v: v)) to give IC-33 (4 g, yield 81%).

¾丽 R: δ 1.20 (s, 6Η), 6.45 (d, 1H) , 7.25 (d, 1Η), 7.37 (m, 3H) , 7.49 (d, 1H), 7.75 (d, 1H), 7.86 (d, 1H), 8.22 (s, 1H)  ¾ 丽 R: δ 1.20 (s, 6Η), 6.45 (d, 1H), 7.25 (d, 1Η), 7.37 (m, 3H), 7.49 (d, 1H), 7.75 (d, 1H), 7.86 (d , 1H), 8.22 (s, 1H)

[준비예 34] IC-34의 합성  Preparation Example 34 Synthesis of IC-34

<단계 1> 4-(2-benzhydrylphenyl)-lH-indole의 합성  <Step 1> Synthesis of 4- (2-benzhydrylphenyl) -lH-indole

Figure imgf000185_0002
Figure imgf000185_0002

5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indole 대신 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-indoIe을 사용하고 l-bromo-2-ni trobenzene 대신 (2— bromophenyl )methylene)dibenzene을사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 4- ( 2-benzhydr y 1 pheny 1 ) - 1H- i ndo 1 e을 얻었다. 5- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indole instead Use 4- (4,4,5,5-tetramethyl-l, 3,2-dioxaborolan-2-yl) -lH-indoIe and use (2—bromophenyl) methylene) dibenzene instead of l-bromo-2-ni trobenzene Except for using the same procedure as in <Step 2> of Preparation Example 1 to obtain 4- (2-benzhydr y 1 pheny 1)-1H- i ndo 1 e.

¾ NMR: δ 2.88 (m, 1H), 6.44 (d, 1H), 7.27 (m, 6H), 7.34 (m, 8H), 7.47 (d, 1H), 7.75 (m, 2H) , 7.86 (d, 1H), 8.21 (s, 1H)  ¾ NMR: δ 2.88 (m, 1H), 6.44 (d, 1H), 7.27 (m, 6H), 7.34 (m, 8H), 7.47 (d, 1H), 7.75 (m, 2H), 7.86 (d, 1H), 8.21 (s, 1H)

<단계 2> IC-34의 합성  <Step 2> Synthesis of IC-34

Figure imgf000186_0001
Figure imgf000186_0001

4-(2-isopropylphenyl)-lH-indole 대신 상기 <단계 1>에서 얻은 4- (2-benzhydryl pheny 0-1H- indole을 사용하여 준비예 11의 <단계 2>와 동일한 과정올 수행하여 IC-34을 얻었다.  Using the 4- (2-benzhydryl pheny 0-1H-indole obtained in <Step 1> instead of 4- (2-isopropylphenyl) -lH-indole, the same procedure as in <Step 2> of Preparation Example 11 was performed. 34 was obtained.

¾匪 R: δ 6.43 (d, 1H), 7.26 (m, 5H), 7.34 (m, 8H), 7.46 (d, 1H), 7.76 (m, 2H), 7.85 (d, 1H), 8.20 (s, 1H)  ¾ 匪 R: δ 6.43 (d, 1H), 7.26 (m, 5H), 7.34 (m, 8H), 7.46 (d, 1H), 7.76 (m, 2H), 7.85 (d, 1H), 8.20 (s , 1H)

[준비예 35] IC-35의 합성  Preparation 35 Synthesis of IC-35

<단계 1> 6- (2-bromophenyl )-그 chloro-lH- indole의 합성  <Step 1> Synthesis of 6- (2-bromophenyl) -chloro-lH-indole

Figure imgf000186_0002
Figure imgf000186_0002

질소 기류 하에서 9.13 g (39.6mmol)의 6-bromo-7_chloro—lH— indole, 9.54 g (47.5隱 ol)의 2-bromophenylboronic acid, 4.75 g (118.8隱 ol)의 NaOH과 200 ml/ 100 ml의 THF/H20를 넣고 교반하였다. 40°C에서 2.29 g (5 mol%)의 Pd(PPh3)4를 넣고 80°C에서 12시간 동안 교반하였다. 반웅 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 6-(2-bromophenyl)— 7-chloro-lH-indole 8.86 g (28.9 mmol, yield: 73 %)을 획득하였다.9.13 g (39.6 mmol) of 6-bromo-7_chloro—lH— indole, 9.54 g under nitrogen stream (47.5 bor ol) of 2-bromophenylboronic acid, 4.75 g (118.8 隱 ol) of NaOH, and 200 ml / 100 ml of THF / H 2 0 were added and stirred. At 40 ° C into a Pd (PPh 3) 4 of 2.29 g (5 mol%) was stirred at 80 ° C for 12 hours. After completion of reaction, the mixture was extracted with methylene chloride and filtered with MgS0 4 . 8.86 g (28.9 mmol, yield: 73%) of the target compound 6- (2-bromophenyl)-7-chloro-lH-indole was obtained by removing the solvent of the filtered organic layer using column chromatography.

-匪 R ： δ 6.45 (d, 1H), 7.35 (m, 3H), 7.74 (m, 3H)， 8.06 (d, 1H), 8.64 -匪 R: δ 6.45 (d, 1H), 7.35 (m, 3H), 7.74 (m, 3H), 8.06 (d, 1H), 8.64

(s, 1H) (s, 1H)

<단계 2> ethyl 3-(2-(7-chloro— lH-indol-6-yl henyl thio ropanoate의 합성  <Step 2> Synthesis of ethyl 3- (2- (7-chloro— lH-indol-6-yl henyl thio ropanoate

Figure imgf000187_0001
Figure imgf000187_0001

질소 기류 하에서 7.45 g (24.3 隱 ol)의 7.45 g (24.3 隱 ol) under a stream of nitrogen

6- ( 2-br omopheny 1 ) -7-ch 1 or o- 1H- i ndo 1 e , 3.59 g (26.77 画 ol)의 ethyl 3-mercaptopropanoate, 167 mg (0.18誦 ol)의 Pd2dba3 , 197 mg (0.37 mmol)의 dpephos , 8.4 g (61 mmol)의 K2C03를 100 ml의 Toluene에 넣고 110°C에서 15시간 교반하였다. 반웅 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 ethyl 3-(2-(7-chloro-lH-indol-6~yl )phenylthio)propanoate 6.38 g (17.7 mmol , yield: 72 %)을 획득하였다. 6- (2-br omopheny 1) -7-ch 1 or o- 1H- i ndo 1 e, 3.59 g (26.77 画 ol) ethyl 3-mercaptopropanoate, 167 mg (0.18 誦 ol) Pd2dba 3 , 197 mg (0.37 mmol) of dpephos and 8.4 g (61 mmol) of K 2 CO 3 were added to 100 ml of Toluene and stirred at 110 ° C. for 15 hours. After completion of reaction, the mixture was extracted with methylene chloride and filtered with MgS0 4 . 6.38 g (17.7 mmol, yield: 72%) of the target compound, ethyl 3- (2- (7-chloro-lH-indol-6 ~ yl) phenylthio) propanoate, was removed by removing the solvent of the filtered organic layer using column chromatography. Obtained.

:H-NMR ： δ 1.29 (t, 3Η), 2.58 (t, 2H), 3.12 (t, 2H)， 4.12 (q, 2H) , 6.25 (d, 1H)' 7.37 (m, 4H), 7.70 (m, 2H), 8.06 (d, 1H), 8.60 (s, 1H) <단계 3> IC-35의 합성 : H-NMR: δ 1.29 (t, 3Η), 2.58 (t, 2H), 3.12 (t, 2H), 4.12 (q, 2H), 6.25 (d, 1H) '7.37 (m, 4H), 7.70 ( m, 2H), 8.06 (d, 1H), 8.60 (s, 1H) <Step 3> Synthesis of IC-35

Figure imgf000188_0001
Figure imgf000188_0001

질소 기류 하에서 6.34 g (15.4 画 ol)의 ethyl 3- ( 2-( 7-ch 1 or o-lH- i ndo 1 -6-y 1 )pheny 11 h i o)pr opanoat e , 2.60 g (23.2 薩 ol)의 potassium tert-butoxide를 100 ml의 THF에 넣고 50°C에서 8시간 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한후 컬럼크로마토그래피를 이용하여 IC-352.30 g (10.3 mmol, yield: 67 %)을 획득하였다. 6.34 g (15.4 画 ol) of ethyl 3- (2- (7-ch 1 or o-lH- i ndo 1 -6-y 1) pheny 11 hio) pr opanoat e, 2.60 g (23.2 薩 ol) under nitrogen stream ) Potassium tert-butoxide was added to 100 ml of THF and stirred at 50 ° C for 8 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgS0 4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer was obtained IC-352.30 g (10.3 mmol, yield: 67%) by column chromatography.

¾-NMR ： δ 6.44 (d, 1H), 7.25 (d, 1H) , 7.51 (m, 3H), 8.00 (m, 2H), 8.40 (d, 1H), 8.63 (s, 1H)  ¾-NMR: δ 6.44 (d, 1H), 7.25 (d, 1H), 7.51 (m, 3H), 8.00 (m, 2H), 8.40 (d, 1H), 8.63 (s, 1H)

[준비예 36] IC-36의 합성  Preparation 36 Synthesis of IC-36

<단계 1> 5-(2-bromophenyl)-6-chlor으 LH-indole의 합성  Step 1 Synthesis of LH-indole with 5- (2-bromophenyl) -6-chlor

Figure imgf000188_0002
Figure imgf000188_0002

6ᅳ bromoᅳ 7_chloroᅳ 1Hᅳ indole 대신 5一 bromoᅳ 6ᅳ chloroᅳ 1Hᅳ indole 9.13 g (39.6 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 1>과 동일한 과정을 수행하여 5- ( 2-br omopheny 1 ) -6~ch 1 or o- 1H- i ndo 1 e 8.62 g (28.1 mmol, yield ： 71%)을 얻었다.Except for using 513 bromo ᅳ 6 ᅳ chloro ᅳ 1H ᅳ indole 9.13 g (39.6 mmol) instead of 6 ᅳ bromo ᅳ 7_chloro ᅳ 1H ᅳ indole, (2-br omopheny 1) -6 ~ ch 1 or o-1 H- i ndo 1 e 8.62 g (28.1 mmol, yield: 71%) Got it.

-NMR ： δ 6.44 (d, 1H) , 7.34 (m, 4H)， 7.61 (m, 3H) , 8.59 (s, 1H)  -NMR: δ 6.44 (d, 1H), 7.34 (m, 4H), 7.61 (m, 3H), 8.59 (s, 1H)

<단계 2> ethyl 3-(2-(6-chloro-lH-indol-5-yl)phenylthio)propanoate의 합성  <Step 2> Synthesis of ethyl 3- (2- (6-chloro-lH-indol-5-yl) phenylthio) propanoate

Figure imgf000189_0001
Figure imgf000189_0001

6ᅳ ( 2-bromopheny l)-7-chloro- 1H- i ndo le 대신 5- ( 2-br omopheny 1 ) -6-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 瞧 ol)을 사용하는 것을 제외하고는 준비예 35의 <단계 2>와 동일한 과정을 수행하여 ethyl 3- ( 2-(6-ch 1 or o-lH- i ndo 1 -5-y 1 )pheny 11 h i o )pr opanoat e 6.73 g (18.71 mmol , yield ： 77«을 얻었다.  Instead of 6 ᅳ (2-bromopheny l) -7-chloro- 1H- i ndo le, instead of 5- (2-br omopheny 1) -6-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 瞧 ol) Except for using, the same procedure as in <Step 2> of Preparation Example 35 was carried out to obtain ethyl 3- (2- (2- (6-ch 1 or o-lH- i ndo 1 -5-y 1) pheny 11 hio) pr Opanoat e 6.73 g (18.71 mmol, yield: 77 «was obtained.

¾-NMR ： δ 1.29 (t, 3Η), 2.58 (t, 2H), 3.17 (t, 2H), 4.13 (q, 2H), 6.35 (d, 1H), 7.39 (m, 5H), 7.70 (m, 2H), 8.64 (s, 1H)  ¾-NMR: δ 1.29 (t, 3Η), 2.58 (t, 2H), 3.17 (t, 2H), 4.13 (q, 2H), 6.35 (d, 1H), 7.39 (m, 5H), 7.70 (m , 2H), 8.64 (s, 1H)

<단계 3> IC-36의 합성  Step 3 Synthesis of IC-36

Figure imgf000189_0002
Figure imgf000189_0002

ethyl 3-(3-(2-chloro-9H-carbazol~3-yl )pyr idin-2-ylthio)propanoate 대신 ethyl 3-(2-(6-chloro-lH-indol-5-yl )phenylthio)propanoate 6.34g (15.4 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 3>와 동일한 과정을 수행하여 IC-36 2.44 g (10.9 mmol, yield ： 71 를 얻았다. ethyl 3- (2- (6-chloro-lH-indol-5-yl) phenylthio) propanoate instead of ethyl 3- (3- (2-chloro-9H-carbazol ~ 3-yl) pyr idin-2-ylthio) propanoate Except for using 6.34 g (15.4 mmol), IC-36 was carried out in the same manner as in <Step 3> of Preparation Example 35. 2.44 g (10.9 mmol, yield: 71) were obtained.

¾-NMR ： δ 6.50 (d, 1H), 7.51 (m, 3H) , 7.71 (d, 1H) , 8.01 (m, 2H), 8.45 (d, 1H), 8.68 (s, 1H)  ¾-NMR: δ 6.50 (d, 1H), 7.51 (m, 3H), 7.71 (d, 1H), 8.01 (m, 2H), 8.45 (d, 1H), 8.68 (s, 1H)

[준비예 37] IC-37의 합성  Preparation Example 37 Synthesis of IC-37

〈단계 1> 4- ( 2-br omopheny 1 ) -5-ch 1 or o- 1H- i ndo 1 e 의 합성  <Step 1> Synthesis of 4- (2-br omopheny 1) -5-ch 1 or o- 1H- i ndo 1 e

Figure imgf000190_0001
Figure imgf000190_0001

6ᅳ bromo一 7ᅳ chloroᅳ 1Hᅳ indole 대신 4-br omo-5-ch 1 or ο~1Η- i ndo 1 e 9.13 g (39.6 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 1>과 동일한 과정을 수행하여 4- ( 2-br omopheny 1 ) -5-ch 1 or ο-1Η- i ndo 1 e 8.50 g (27.7 mmol, yield ： 70%)을 얻었다. . <Step 1 of Preparation Example 35 except that 4-br omo-5-ch 1 or ο ~ 1Η- i ndo 1 e 9.13 g (39.6 mmol) was used instead of 6 ᅳ bromo 一 7 ᅳ chloro ᅳ 1H ᅳ indole. 8.50 g (27.7 mmol, yield: 70%) of 4- (2-br omopheny 1) -5-ch 1 or ο-1Η- i ndo 1 e was obtained by the same procedure as>. .

¾-NMR ： δ 6.48 (d, 1H), 7.39 (m, 4H), 7.62 (m, 3H), 8.61 (s, 1H)  ¾-NMR: δ 6.48 (d, 1H), 7.39 (m, 4H), 7.62 (m, 3H), 8.61 (s, 1H)

<단계 2> ethyl 3-(2-(5-chloro-lH-indo卜 4-yl)phenylthio)propanoate의 합성  <Step 2> Synthesis of ethyl 3- (2- (5-chloro-lH-indo 卜 4-yl) phenylthio) propanoate

Figure imgf000190_0002
Figure imgf000190_0002

4- ( 2-br omopheny 1 ) -5-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 麵 ol)을 사용하는 것을 제외하고는 준비예 35의 <단계 2>와 동일한 과정을 수행하여 ethyl 3- ( 2- ( 5-ch 1 or o-lH- i ndo 1 -4-y 1 ) pheny 11 h i o ) r opanoat e 6.56 g (18.2 mmol , yield ： 75%)을 얻었다. Perform the same procedure as in <Step 2> of Preparation Example 35, except that 4- (2-br omopheny 1) -5-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 麵 ol) is used. Ethyl 3- (2- (5-ch 1 or o-lH- i ndo 1 -4-y 1) pheny 11 hio) r opanoat e 6.56 g (18.2 mmol, yield: 75%).

¾-NMR ： δ 1.28 (t, 3H), 2.58 (t, 2H)， 3.11 (t, 2H), 4.12 (q, 2H), 6.27 (d, 1H), 7.27 (m, 4H), 7.55 (m, 3H), 8.61 (s, 1H)  ¾-NMR: δ 1.28 (t, 3H), 2.58 (t, 2H), 3.11 (t, 2H), 4.12 (q, 2H), 6.27 (d, 1H), 7.27 (m, 4H), 7.55 (m , 3H), 8.61 (s, 1H)

<단계 3> IC-37의 합성  Step 3 Synthesis of IC-37

Figure imgf000191_0001
Figure imgf000191_0001

ethyl 3-(3-(2-chloro-9H-carbazol-3-yl )pyr idi η-2-y 1 thi o)propanoat e 대신 ethyl 3-(2-(5-chloro~ 1H- i ndo 1 -4-y 1 ) pheny 11 h i o ) pr opanoa t e 6.34g (15.4 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 3>와 동일한 과정을 수행하여 IC-37 2.68 g (12.0瞧 01， yield ： 78 %)를 얻었다. ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyr idi η-2-y 1 thi o) propanoate instead of ethyl 3- (2- (5-chloro ~ 1H- i ndo 1- 4-y 1) pheny 11 hio) The same procedure as in <Step 3> of Preparation Example 35 was carried out except for the use of 6.34 g (15.4 mmol) of pr opanoa te and 2.68 g (12.0 瞧0 1 ， yield: 78%).

一丽 R ： δ 6.50 (d, 1H), 7.31 (m, 2H)， 7.51 (m, 2H), 8.01 (m, 2H), 8.44 (d, 1H), 8.58 (s, 1H)  一 丽 R ： δ 6.50 (d, 1H), 7.31 (m, 2H), 7.51 (m, 2H), 8.01 (m, 2H), 8.44 (d, 1H), 8.58 (s, 1H)

[준비예 38] IC-38의 합성  Preparation 38 Synthesis of IC-38

<단계 1> 7-(2-bromophenyl)-6-chloro-lH-indole의 합성  Step 1 Synthesis of 7- (2-bromophenyl) -6-chloro-lH-indole

Figure imgf000191_0002
Figure imgf000191_0002

6-br omo-7-ch 1 or o- 1H- i ndo 1 e 대신 7ᅳ broracH5_chloro一 1Hᅳ indole 9.13 g (39.6 誦 o 1)을 사용하는 것을 제외하고는 준비예 35의 <단계 1>과 동일한 과정을 수행하여 7-( 2-br oraopheny 1 ) -6-ch 1 or ο-1Η- i ndo 1 e 9.59 g (31.3 mmol, yield ： 79D을 얻었다.Except for using 9-7 broracH5_chloro 一 1H n indole 9.13 g (39.6 誦 o1) instead of 6-br omo-7-ch 1 or o- 1H- i ndo 1 e 9.59 g (31.3 mmol, yield ： 79D of 7- (2-br oraopheny 1) -6-ch 1 or ο-1Η- i ndo 1 e Got it.

-蘭 R ： δ 6.48 (d, 1Η)' 7.06 (d, 1Η), 7.33 (m, 3H) , 7.62 On, 2H)， 8.01 (d, 1H), 8.71 (s, 1H)  -蘭 R: δ 6.48 (d, 1Η) '7.06 (d, 1Η), 7.33 (m, 3H), 7.62 On, 2H), 8.01 (d, 1H), 8.71 (s, 1H)

<단계 2> ethyl 3-(2-(6-chloro_lH-indol-7-yl )phenylthio)propanoate의 합성  <Step 2> Synthesis of ethyl 3- (2- (6-chloro_lH-indol-7-yl) phenylthio) propanoate

Figure imgf000192_0001
Figure imgf000192_0001

6-(2-bromophenyl )ᅳ그 chlor으 1Hᅳ indole 대신 7- ( 2-br omopheny l)-6-chloro-lH-indole 7.45 g (24.3 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 2>와 동일한 과정을 수행하여 ethyl 3-(2-(6-chloro-lH-indol-7-yl )phenyl thio)propanoate 6.47 g (18.0 mmol , yield ： 74%)을 얻었다. <Step of Preparation 35, except that 7- (2-bromopheny l) -6-chloro-lH-indole 7.45 g (24.3 mmol) was substituted for 1-H indole for 6- (2-bromophenyl) group chlor. 2.47 g (18.0 mmol, yield: 74%) of ethyl 3- (2- (6-chloro-lH-indol-7-yl) phenyl thio) propanoate was obtained in the same manner as in 2>.

-NMR ： δ 1.29 (t, 3H), 2.58 (t, 2H)， 3.13 (t, 2H) , 4.12 (q, 2H) , 6.24 (d, 1H), 7.06 (d, 1H), 7.27 (m, 3H), 7.70 (m, 2H), 8.00 (d, 1H), 8.61 (s, 1H) <단계 3> IC-38의 합성  -NMR: δ 1.29 (t, 3H), 2.58 (t, 2H), 3.13 (t, 2H), 4.12 (q, 2H), 6.24 (d, 1H), 7.06 (d, 1H), 7.27 (m, 3H), 7.70 (m, 2H), 8.00 (d, 1H), 8.61 (s, 1H) <Step 3> Synthesis of IC-38

Figure imgf000192_0002
Figure imgf000192_0002

ethyl 3-(3-(2-chloro-9H-carbazol-3-yl ) pyr i d i η-2-y 11 h i o ) pr opanoa t e 대신 ethyl 3-(2-(6-chloro~ 1H- i ndo 1 -7-y 1 ) heny 11 h i o ) r opanoa t e 6.34g (15.4 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 3〉와 동일한 과정을 수행하여 IC-38 2.48 g (11.1 mmol, yield ： 72 ¾)를 얻었다.ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyr idi η-2-y 11 hio) instead of pr opanoa te ethyl 3- (2- (6-chloro ~ 1H- i ndo 1- 7-y 1) heny 11 hio) r Opanoa te 6.34g (15.4 mmol) was used, but the same procedure as in <Step 3> of Preparation Example 35 was performed. 2.48 g (11.1 mmol, yield: 72 ¾) were obtained.

-NMR ： δ 6.44 (d, 1H), 7.51 (m, 4H), 7.89 (m, 2H)， 8.48 (d, 1H) , 8.68 -NMR: δ 6.44 (d, 1H), 7.51 (m, 4H), 7.89 (m, 2H), 8.48 (d, 1H), 8.68

(s, 1H) (s, 1H)

[준비예 39] IC-39의 합성  Preparation 39 Synthesis of IC-39

〈단계 1> 6-(2-bronK)phenyl)-5-chloro-lH-indole의 합성  <Step 1> Synthesis of 6- (2-bronK) phenyl) -5-chloro-lH-indole

Figure imgf000193_0001
Figure imgf000193_0001

6-bromo-7-chloro~lH- indole 대신 6ᅳ bromoᅳ 5ᅳ chloro一 1Hᅳ indole 9.13 g (39.6 隱 ol)올 사용하는 것을 제외하고는 준비예 35의 <단계 1>과 동일한 과정올 수행하여 6- ( 2-bromopheny 1 ) -5-ch 1 or o- 1H- i ndo 1 e 8.13 g (26.5 mmol, yield ： 67%)을 얻었다. Perform the same procedure as in <Step 1> of Preparation Example 35, except for using 6 ᅳ bromo ᅳ 5 ᅳ chloro 一 1H ᅳ indole 9.13 g (39.6 隱 ol) instead of 6-bromo-7-chloro to lH-indole. 8.13 g (26.5 mmol, yield: 67%) of 6- (2-bromopheny 1) -5-ch 1 or o-1H-i ndo 1 e was obtained.

¾-NMR ： δ 6.45 (d, 1H), 7.29 (m, 3H) , 7.62 (m, 4H), 8.71 (s, 1H)  ¾-NMR: δ 6.45 (d, 1H), 7.29 (m, 3H), 7.62 (m, 4H), 8.71 (s, 1H)

<단계 2> ethyl 3-(2-(5-chloro-lH-indol-6-yl )phenylthio)propanoate의 합성  <Step 2> Synthesis of ethyl 3- (2- (5-chloro-lH-indol-6-yl) phenylthio) propanoate

Figure imgf000193_0002
Figure imgf000193_0002

6- (2-bromopheny 1 )一그 ch loro- 1H- i ndo 1 e 대신 6- (2-bromopheny 1) one ch loro- 1 H- i ndo 1 e instead

6- ( 2-bromopheny 1 ) -5-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 瞧 ol)을 사용하는 것을 제외하고는 준비예 35의 <단계 2>와 동일한 과정을 수행하여 ethyl ethyl 3- ( 2- ( 5-ch 1 or o- 1H- i ndo 1 -6-y l)phenylthio)propanoate 7.00 g (19.4 mmol , yield ： 81«올 얻었다. Except for using 6- (2-bromopheny 1) -5-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 瞧 ol), the same procedure as in <Step 2> of Preparation Example 35 was performed. ethyl ethyl 3- (2- (5-ch 1 or o-1H-i ndo 1 -6-yl) phenylthio) propanoate 7.00 g (19.4 mmol, yield ： 81 «got it.

¾-NMR ： δ 1.29 (t, 3H), 2.58 (t, 2H) , 3.12 (t, 2H) , 4.13 (q, 2H)， 6.26 (d, 1H), 7.37 Cm, 4H)， 7.66 (m, 3H) , 8.61 (s, 1H)  ¾-NMR: δ 1.29 (t, 3H), 2.58 (t, 2H), 3.12 (t, 2H), 4.13 (q, 2H), 6.26 (d, 1H), 7.37 Cm, 4H), 7.66 (m, 3H), 8.61 (s, 1H)

<단계 3> IC-39의 합성  <Step 3> Synthesis of IC-39

Figure imgf000194_0001
Figure imgf000194_0001

ethyl 3-(3-(2-chloro-9H-carbazol-3-yl)pyr idin-2-yl thio)propanoate 대신 ethyl 3-(2-(5-chloro-lH-indol-6-yl )phenylthio)propanoate 6.34g (15.4 瞧 ol)을 사용하는 것을 제외하고는 준비예 35의 <단계 3>와 동일한 과정을 수행하여 IC-39 2.58 g (11.5誦 ol, yield ： 75 %)를 얻었다.  ethyl 3- (2- (5-chloro-lH-indol-6-yl) phenylthio) instead of ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyr idin-2-yl thio) propanoate Except for using 6.34g (15.4 瞧 ol) of propanoate, 2.58 g (11.5 誦 ol, yield: 75%) of IC-39 were obtained by the same procedure as <Step 3> of Preparation Example 35.

¾-NMR ： δ 6.45 (d, 1H), 7.31 (d, 1H), 7.50 (w, 2H), 7.81 (m, 2H) , 8.01 (d, 1H), 8.48 (d, 1H), 8.68 (s, 1H)  ¾-NMR: δ 6.45 (d, 1H), 7.31 (d, 1H), 7.50 (w, 2H), 7.81 (m, 2H), 8.01 (d, 1H), 8.48 (d, 1H), 8.68 (s , 1H)

[준비예 40] IC-40의 합성  Preparation 40 Synthesis of IC-40

<단계 1> 5-(2-bromophenyl)-4-chloro-lH-indole의 합성  <Step 1> Synthesis of 5- (2-bromophenyl) -4-chloro-lH-indole

Figure imgf000194_0002
Figure imgf000194_0002

5ᅳ bromoᅳ 4ᅳ chloroᅳ 1Hᅳ indole 대신 4-br omo-5-ch 1 or ο-1Η- i ndo 1 e 9.13 g (39.6 mmol)을 사용하는 것을 제외하고는 준비예 35의 <단계 1>과 동일한 과정을 수행하여 5- ( 2-br omopheny l)-4-chl or o-lH- indole 8.98 g (29.3 mmol, yield ： 74%)을 얻었다. <Step 1 of Preparation Example 35 except that 4-br omo-5-ch 1 or ο-1Η- i ndo 1 e 9.13 g (39.6 mmol) was used instead of 5 bromo ᅳ 4 ᅳ chloro ᅳ 1H ᅳ indole. > Same process as 8.98 g (29.3 mmol, yield: 74%) of 5- (2-br omopheny l) -4-chl or o-lH-indole was obtained.

¾-NMR ： δ 6.44 (d, 1H), 7.38 (m, 3H), 7.59 (m, 3H), 7.82 (d, 1H) , 8.71 ¾-NMR: δ 6.44 (d, 1H), 7.38 (m, 3H), 7.59 (m, 3H), 7.82 (d, 1H), 8.71

(s, 1H) (s, 1H)

<단계 2> ethyl 3-(2-(4-chloro-lH-indol-5-yl )phenylthio)propanoate의 합성  <Step 2> Synthesis of ethyl 3- (2- (4-chloro-lH-indol-5-yl) phenylthio) propanoate

Figure imgf000195_0001
Figure imgf000195_0001

6-(2~br omopheny 1 ) -7-ch 1 or으 1H- i ndo le 대신 5- ( 2-br omopheny 1 ) -4-ch 1 or o- 1H- i ndo 1 e 7.45 g (24.3 mmol)을 사용하는 것올 제외하고는 준비예 35의 <단계 2>와 동일한 과정을 수행하여 ethyl 3-(2-(4-chloro-lH-indol-5-yl )phenylthio)propanoate 6.82 g (19.0 mmol , yield ： 78%)을 얻었다. 6- (2 ~ bromopheny 1) -7-ch 1 or instead of 1H- i ndo le 5- (2-br omopheny 1) -4-ch 1 or o-1 H- i ndo 1 e 7.45 g (24.3 mmol Except for using), 6.82 g (19.0 mmol, ethyl 3- (2- (4-chloro-lH-indol-5-yl) phenylthio) propanoate was prepared in the same manner as in <Step 2> of Preparation Example 35. yield: 78%).

¾-NMR ： δ 1.30 (t, 3H), 2.58 (t, 2H), 3.12 (tᅳ 2H), 4.11 (q, 2H), 6.25 (d, 1H), 7.33 (in, 4H), 7.65 (m, 3H), 8.61 (s, 1H)  ¾-NMR: δ 1.30 (t, 3H), 2.58 (t, 2H), 3.12 (t ᅳ 2H), 4.11 (q, 2H), 6.25 (d, 1H), 7.33 (in, 4H), 7.65 (m , 3H), 8.61 (s, 1H)

<단계 3> IC-40의 합성  Step 3 Synthesis of IC-40

Figure imgf000195_0002
Figure imgf000195_0002

ethyl 3-(3-(2-chloro-9H-carbazol-3-yl)pyr idin-2-ylthio)propanoate 대신 3- ( 2- ( 4-ch 1 or o- 1H- i ndo 1 -5-y 1 ) pheny 11 h i o )pr opanoat e 6.34g (15.4 瞧 ol)을 사용하는 것을 제외하고는 준비예 35의 <단계 3>와 동일한 과정올 수행하여 IC-40 2.58 g (11.6 瞧 ol, yield ： 75 %)를 얻었다. ethyl 3- (3- (2-chloro-9H-carbazol-3-yl) pyr idin-2-ylthio) propanoate instead of 3- (2- (4-ch 1 or o-1H- i ndo 1 -5-y 1) pheny 11 hio) pr opanoat e 6.34g (15.4 瞧 ol) Except for using the same procedure as in <Step 3> of Preparation Example 35 to obtain 2.58 g (11.6 Pa ol, yield: 75%) IC-40.

¾-NMR ： δ 6.43 (d, 1H), 7.33 (m, 2H), 7.51 (m, 2H)， 7.99 (m, 2H) , 8.48 (d, 1H), 8.68 (s, 1H)  ¾-NMR: δ 6.43 (d, 1H), 7.33 (m, 2H), 7.51 (m, 2H), 7.99 (m, 2H), 8.48 (d, 1H), 8.68 (s, 1H)

[준비예 41] IC-41의 합성  Preparation Example 41 Synthesis of IC-41

〈단계 1> 7-(2-nitrophenyl)benzo[b]thiophene의 합성  <Step 1> Synthesis of 7- (2-nitrophenyl) benzo [b] thiophene

Figure imgf000196_0001
Figure imgf000196_0001

질소 기류 하에서 12.2 g (35.2 画 ol)의 7-bromobenzo[b]thiophene, 6.44 g (38.7酬 ol)의 2-nitrophenylboronic acid, 4.22 g (105.6議 ol )의 NaOH과 300 ml/ 150 ml의 THF/H20를 넣고 교반하였다. 40°C에서 2.03 g (5 mol%)의 Pd(PPh3)4를 넣고 80°C에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 7-(2-ni trophenyl )benzo[b] thiophene 7.38 g (28.9 隱 ol, yield 82 «을 획득하였다.12.2 g (35.2 μl) of 7-bromobenzo [b] thiophene, 6.44 g (38.7 μl) of 2-nitrophenylboronic acid, 4.22 g (105.6 μl) of NaOH and 300 ml / 150 ml of THF / H 2 0 was added and stirred. At 40 ° C into a Pd (PPh 3) 4 of 2.03 g (5 mol%) was stirred at 80 ° C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgS0 4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer using a column chromatography to obtain 7.38 g (28.9 «ol, yield 82« 7- (2-ni trophenyl) benzo [b] thiophene.

-丽 R ： δ 7.63 (m, 5H) , 7.96 (m, 3H), 8.21 (d, 1H)  -丽 R: δ 7.63 (m, 5H), 7.96 (m, 3H), 8.21 (d, 1H)

<단계 2> IC— 41의 합성  <Step 2> Synthesis of IC—41

Figure imgf000196_0002
질소 기류 하에서 그 (2-nitrophenyl)benzo[b]thiophene 5.53 g (21.7 mmol)과 triphenylphosphine 14.2 g (54.2 mmol) , 1 , 2-d i ch 1 or obenzene 100 ml를 넣은 후 12시간 교반하였다. 반웅 종료 후 1， 2-d ich lor obenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층은 MgS04로 물을 제거하고， 컬럼크로마토그래피를 이용하여 목적 화합물인 IC-41 3.29 g, (14.8 mmol, yield ： 68 «을 획득하였다.
Figure imgf000196_0002
5.53 g (21.7 mmol) of the (2-nitrophenyl) benzo [b] thiophene and 14.2 g (54.2 mmol) of triphenylphosphine, 1, 2-dich 1 or obenzene were added under a nitrogen stream, followed by stirring for 12 hours. After the reaction, 1, 2-d ich lor obenzene was removed and extracted with dichloromethane. The extracted organic layer was water-removed with MgSO 4 , and column chromatography was used to obtain 3.29 g, (14.8 mmol, yield: 68 «) of the target compound, IC-41.

匪 R ： δ 7.37 (t, 1H), 7.46 (m, 5H) , 7.87 (d, 1H) , 8.20 (d, 1H) , 8.24 匪 R: δ 7.37 (t, 1H), 7.46 (m, 5H), 7.87 (d, 1H), 8.20 (d, 1H), 8.24

(s, 1H) (s, 1H)

[준비예 42] IC-42a및 IC-42b의 합성  Preparation Example 42 Synthesis of IC-42a and IC-42b

<단계 1> 6— (2— nitrophenyl)benzo[b]thiophene의 합성  Step 1 Synthesis of 6— (2—nitrophenyl) benzo [b] thiophene

Figure imgf000197_0001
Figure imgf000197_0001

7一 bromobenzo [b] thi ophene 대신 6-br omobenzo [b] thi ophene 12.2 g (35.2 謹 ol)을 사용하는 것을 제외하고는 준비예 41의 <단계 1>과 동일한 과정을 수행하여 6- ( 2- i t r opheny 1 ) benzo [ b ] t h i ophene 7.01 g (27.5 mmol, yield ： 78%)을 얻었다.  Perform the same procedure as in <Step 1> of Preparation Example 41, except that 12.2 g (35.2 謹 ol) of 6-br omobenzo [b] thi ophene is used instead of 7 一 bromobenzo [b] thi ophene. Iter opheny 1) obtained benzo [b] thi ophene 7.01 g (27.5 mmol, yield: 78%).

H-NMR ： δ 7.68 (m, 3H)， 7.98 (ni, 6H)  H-NMR: δ 7.68 (m, 3H), 7.98 (ni, 6H)

<단계 2> IC-42a 및 IC-42b의 합성 Step 2 Synthesis of IC-42a and IC-42b

Figure imgf000198_0001
Figure imgf000198_0001

IC-42D  IC-42D

7-(2-nitr opheny 1 )benzo[b] thi ophene 대신Instead of 7- (2-nitr opheny 1) benzo [b] thi ophene

6- ( 2-n i t r opheny 1 ) benz o [ b ] t h i ophene 5.53 g (21.7 隱 ol)을 사용하는 것을 제외하고는 준비예 41의 <단계 2>와 동일한 과정올 수행하여 IC— 42a 1.60 g (7.16 隱 ol, yield ： 33 ) 과 IC-42b 1.79 g (8.03 mmol, yield ： 37%)을 얻었다. 6- (2-nitr opheny 1) benz o [b] thi ophene 5.53 g (21.7 隱 ol), except that the same procedure as in <Step 2> of Preparation Example 41 was performed. 7.16 隱 ol, yield: 33) and IC-42b 1.79 g (8.03 mmol, yield: 37%) were obtained.

IC-42a의 -丽 R： δ 7.27 (t, IH), 7.53 (m, 41ᅳ 1)， 7.78 (d, IH) , 7.92 (d, IH) , 8.10 (d, IH), 8.25 (s, IH)  IC-42a's R: δ 7.27 (t, IH), 7.53 (m, 41 ᅳ 1), 7.78 (d, IH), 7.92 (d, IH), 8.10 (d, IH), 8.25 (s, IH)

IC-42b의 -丽 R： δ 7.29 (t, IH)， 7.63 (m, 3H) , 7.79 (m, 3H)， 8.11 (d, IH) , 8.25 (s, IH)  IC-42b-丽 R: δ 7.29 (t, IH), 7.63 (m, 3H), 7.79 (m, 3H), 8.11 (d, IH), 8.25 (s, IH)

[준비예 43] IC-43의 합성  Preparation Example 43 Synthesis of IC-43

<단계 1> 4-(2-nitrophenyl)benzo[b]thiophene의 합성  <Step 1> Synthesis of 4- (2-nitrophenyl) benzo [b] thiophene

Figure imgf000198_0002
Figure imgf000198_0002

7-bromobenzo[b] thi ophene 대신 4-bromobenzo[b] thi ophene 12.2 g (35.2 睡 ol)을 사용하는 것을 제외하고는 준비예 41의 <단계 1>과 동일한 과정을 수행하여 4- ( 2-n i t r opheny 1 ) benzo [ b ] t h i ophene 7.28 g (28.5 mmol , yield ： 81%)을 얻었다.Except for using 12.2 g (35.2 op ol) of 4-bromobenzo [b] thi ophene instead of 7-bromobenzo [b] thi ophene, the same procedure as in <Step 1> of Preparation Example 41 was performed. nitr opheny 1) benzo [b] thi ophene 7.28 g (28.5 mmol, yield: 81%) Got it.

-丽 R ： δ 7.68 (m, 4H), 7.89 (m, 3H), 8.01 (m, 2H)  -丽 R: δ 7.68 (m, 4H), 7.89 (m, 3H), 8.01 (m, 2H)

<단계 2〉 IC-43의 합성  Step 2 Synthesis of IC-43

Figure imgf000199_0001
Figure imgf000199_0001

7-(2-nitrophenyl ) benzo [blthi ophene 대신 4-(2-nitrophenyl)benzo[b]thiophene 5.53 g (21.7 nrniol)을 사용하는 것을 제외하고는 준비예 41의 <단계 2>와 동일한 과정을 수행하여 IC-43 3.05 g (13.7 瞧 ol, yield ： 63 ¾>)을 얻었다.  Perform the same procedure as in <Step 2> of Preparation Example 41, except that 5.53 g (21.7 nrniol) of 4- (2-nitrophenyl) benzo [b] thiophene is used instead of 7- (2-nitrophenyl) benzo [blthi ophene]. IC-43 3.05 g (13.7 瞧 ol, yield: 63 ¾>) was obtained.

¾-NMR ： δ 7.31 (m, 2H)， 7.73 (m, 4H), 7.96 (d, 1H), 8.10 (d, 1H) , 8.26 ¾-NMR: δ 7.31 (m, 2H), 7.73 (m, 4H), 7.96 (d, 1H), 8.10 (d, 1H), 8.26

(s, 1H) (s, 1H)

[준비예 44] IC-44의 합성  Preparation Example 44 Synthesis of IC-44

<단계 1> ( 6~br omod i benzo [b , d ] t h i ophen-4-y 1 ) t r i methy 1 s i 1 ane≤ 합성

Figure imgf000199_0002
<Step 1> (6 ~ br omod i benzo [b, d] thi ophen-4-y 1) tri methy 1 si 1 ane ≤ synthesis
Figure imgf000199_0002

질소 기류 하에서 17.1 g (50.0 mmol)의 4,6_dibroraodibenzo[b,cl]thiophene를 THF 300 ml 에 녹인 후， _78°C에서 n-butyl lithium (2.5 M in hexane) 19.6 ml (50.0 讓 ol)을 천천히 넣은 후 30분 뒤 상온에서 1시간 동안 교반하고， chlorotrimethylsilane 5.43 g (50.0隱 ol)을 넣고 상온에서 12시간 교반 하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피- 이용하여Dissolve 17.1 g (50.0 mmol) of 4,6_dibroraodibenzo [b, cl] thiophene in 300 ml of THF under a stream of nitrogen and slowly add 19.6 ml (50.0 μl) of n-butyl lithium (2.5 M in hexane) at _78 ° C. After 30 minutes, the mixture was stirred at room temperature for 1 hour, chlorotrimethylsilane 5.43 g (50.0 隱 ol) was added thereto, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgS0 4 was added, and the mixture was filtered. Filtered After removing the solvent of the organic layer using column chromatography-

( 6-br omod i benzo [ b , d ] t h i ophen-4-y 1 ) t r i me t hy 1 s i 1 ane 10.2 g (30.5 mmol , yield(6-br omod i benzo [b, d] t h i ophen-4-y 1) t r i me t hy 1 s i 1 ane 10.2 g (30.5 mmol, yield

61%)을 얻었다.61%).

-應 R ： δ 0.27 (s, 9H), 7.48 (m, 4H)， 8.41 (m, 2H)  -應 R: δ 0.27 (s, 9H), 7.48 (m, 4H), 8.41 (m, 2H)

<단계 2> 6-(trimethylsilyl)dibenzo[b,d]thioi±en-4-aniine의 합성  Step 2 Synthesis of 6- (trimethylsilyl) dibenzo [b, d] thioi ± en-4-aniine

Figure imgf000200_0001
Figure imgf000200_0001

질소 기류 하에서 10.1 (30.0 mmol)의 10.1 (30.0 mmol) under nitrogen stream

( 6~br omod i benzo [ b , d ] t h i ophen-4-y Dtrimethylsil ane을 To 1 uene 100 ml 에 녹인 早， 28 % aqueous ammonia 10.2 ml (150 mmol) 과 Cu 0.10 g (5 mol%)를 넣고, 110°C에서 12시간 동안 교반하였다. 반옹 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기충의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 6-(tr imethylsi lyl )dibenzo[b,d]thiophen-4-amine 6.60 g (24.3 mmol , yield： 81%)을 얻었다.(6 ~ br omod i benzo [b, d] thi ophen-4-y Dtrimethylsil ane dissolved in 100 ml of To 1 uene, 10.2 ml (150 mmol) of 28% aqueous ammonia and 0.10 g (5 mol%) of Cu) After stirring, the mixture was stirred for 12 hours at 110 ° C. After completion of the reaction, the mixture was extracted with methylene chloride and filtered with MgSO 0 4 After removing the solvent of the filtered organic insect, 6- (tr imethylsi lyl) dibenzo [ 6.60 g (24.3 mmol, yield: 81%) of b, d] thiophen-4-amine were obtained.

-NMR ： δ 0.26 (s, 9H), 5.27 (s, 2H), 6.89 (d, 1H) , 7.29 (t, 1H) , 7.52 (m, 2H), 7.81 (d, 1H), 8.39 (d, 1H)  -NMR: δ 0.26 (s, 9H), 5.27 (s, 2H), 6.89 (d, 1H), 7.29 (t, 1H), 7.52 (m, 2H), 7.81 (d, 1H), 8.39 (d, 1H)

<단계 3> IC-44-1의 합성  Step 3 Synthesis of IC-44-1

Figure imgf000200_0002
질소 기류 하에서 5.43 (20.0 mmol)의 6-(tr imethylsi lyl )dibenzo[b,d]thiophen-4-amine을 0/dioxane (10 ml I 90 ml )에 녹인 후， triethanolammonhim chloride 0.372 g (2 mmol) 과 RuClnH200.052 g (0.2 mmol)과 PPh3 0.158 g (0.6 mmol), SnCl2-2H200.452 g (2 隱 ol)을 넣고， 180°C에서 20시간 동안 교반하였다. 반웅 종결 후 aqueous 5% HC1 에 반응물을 붓고， 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한후 컬럼크로마토그래피를 이용하여 IO44-12.60 g (8.8 mmol, yield： 44%)을 얻었다.
Figure imgf000200_0002
5.43 (20.0 mmol) under nitrogen stream 6- (tr imethylsiyl) dibenzo [b, d] thiophen-4-amine was dissolved in 0 / dioxane (10 ml I 90 ml), followed by 0.372 g (2 mmol) of triethanolammonhim chloride and 00.052 g (0.2 mmol) of RuClnH 2 . 0.158 g (0.6 mmol) of PPh 3 and 00.452 g (2 μl ol) of SnCl 2 -2H 2 were added thereto, followed by stirring at 180 ° C. for 20 hours. After completion of reaction, the reaction mixture was poured into aqueous 5% HC1, extracted with methylene chloride, and filtered with MgS0 4 . After removing the solvent of the filtered organic layer and obtained by column chromatography to give IO44-12.60 g (8.8 mmol, yield: 44%).

一醒 R ： δ 0.26 (s, 9Η), 6.45 (d, 1H)， 7.28 (d, 1H), 7.56 (m, 3H) , 8.09 (d, 1H), 8.41 (d, 1H), 8.65 (s, 1H)  一 醒 R: δ 0.26 (s, 9Η), 6.45 (d, 1H), 7.28 (d, 1H), 7.56 (m, 3H), 8.09 (d, 1H), 8.41 (d, 1H), 8.65 (s , 1H)

<단계 4> IC-44의 합성

Figure imgf000201_0001
Step 4 Synthesis of IC-44
Figure imgf000201_0001

질소 기류 하에서 2.60 g (8.8議 ol)의 ICᅳ 44-1을 CHC13 I AcOH (50 ml / 50 ml) 에 녹인 후, 0°C에서 NBS 1.58 g (8.8 mmol) 을 천천히 넣고, 상온에서 1시간 교반하였다. 반응 종결 후 5% NaHC03 수용액에 반응물을 붓고， 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 IC-442.37 g (7.83 mmol, yield ： 89D올 얻었다. 2.60 g (8.8. Ol) of IC ᅳ 44-1 was dissolved in CHC1 3 I AcOH (50 ml / 50 ml) under nitrogen stream, and slowly added 1.58 g (8.8 mmol) of NBS at 0 ° C, followed by 1 at room temperature. Stirred for time. After completion of the reaction, the reaction mixture was poured into 5% NaHC0 3 aqueous solution, extracted with methylene chloride, and filtered with MgS0 4 . After removal of the solvent of the filtered organic layer, IC-442.37 g (7.83 mmol, yield: 89Dol) was obtained by column chromatography.

¾-NMR ： δ 6.45 (d, 1H), 7.27 (d, 1H), 7.54 (m, 3H)， 8.05 (d, 1H) , 8.40 (d, 1H), 8.65 (s, 1H)  ¾-NMR: δ 6.45 (d, 1H), 7.27 (d, 1H), 7.54 (m, 3H), 8.05 (d, 1H), 8.40 (d, 1H), 8.65 (s, 1H)

[준비예 45] IC-45a및 IC-45b의 합성  Preparation Example 45 Synthesis of IC-45a and IC-45b

<단계 1> (8-bromodibenzo[b,d]thiophen-2-yl)trimethylsilane의 합성

Figure imgf000202_0001
<Step 1> Synthesis of (8-bromodibenzo [b, d] thiophen-2-yl) trimethylsilane
Figure imgf000202_0001

4， 6一 d i bromod i benzo [b,d]thi ophene 대신 2, 8ᅳ d i bromod i benzo [b,d]thi ophene 17.1 g (50.0 mmol)을 사용하는 것을 제외하고는 준비예 44의 <단계 1>과 동일한 과정을 수행하여 ( 8-br omod i benzo [b , d ] t h i ophen-2-y 1 ) t r i met hy 1 s i 1 ane 11.6 g (34.5 mmol, yield ： 69%)을 얻었다.  4, <Step 1 of Preparation Example 44, except that 17.1 g (50.0 mmol) of 2,8 ′ di bromod i benzo [b, d] thi ophene was used instead of 6 一 di bromod i benzo [b, d] thi ophene. 11.6 (8-br omod i benzo [b, d] thi ophen-2-y 1) tri met hy 1 si 1 ane 11.6 g (34.5 mmol, yield: 69%) was obtained.

¾-NMR ： δ 0.25 (s, 9H), 7.48 (m, 2H), 7.96 (m, 4H)  ¾-NMR: δ 0.25 (s, 9H), 7.48 (m, 2H), 7.96 (m, 4H)

〈단계 2> 8-(trimethylsi lyl)dibenzo[b,d]thiophen-2-amine의 합성

Figure imgf000202_0002
<Step 2> Synthesis of 8- (trimethylsiyl) dibenzo [b, d] thiophen-2-amine
Figure imgf000202_0002

( 6~br omod i benz o [ b , d ] t h i ophen-4-y Dtrimethylsi lane 대신 ( 8-br omod ibenzo[b,d]thi ophen-2-y 1 ) t r i me t hy 1 s i 1 ane 10.1 g (30.0 mmol)을사용하는 것을 제외하고는 준비예 44의 <단계 2>과 동일한 과정을 수행하여 8-(tr imethylsi lyl )di benzo [b,d]thiophen-2-amine 6.35 g (23.4 mmol , yield： 78%)을 얻었다. (6 ~ br omod i benz o [b, d] thi ophen-4-y Dtrimethylsi lane instead of (8-br omod ibenzo [b, d] thi ophen-2-y 1) tri me t hy 1 si 1 ane 10.1 6.35 g (23.4 mmol) of 8- (tr imethylsiyl) di benzo [b, d] thiophen-2-amine was prepared by the same procedure as in <Step 2> of Preparation Example 44, except that g (30.0 mmol) was used. yield: 78%).

XH-NMR ： δ 0.26 (s, 9H), 5.26 (s, 2H), 7.48 (m, 3H) , 7.79 (d, 1H), 7.96 (d, 1H), 8.01 (s, 1H) X H-NMR: δ 0.26 (s, 9H), 5.26 (s, 2H), 7.48 (m, 3H), 7.79 (d, 1H), 7.96 (d, 1H), 8.01 (s, 1H)

<단계 3> IC-45a-l 및 IC-45b_l의 합성

Figure imgf000203_0001
Step 3 Synthesis of IC-45a-l and IC-45b_l
Figure imgf000203_0001

6-(tr imethylsi lyl )d i benzo [b , d] thi ophen-4-am i ne 대신 Instead of 6- (tr imethylsi lyl) d i benzo [b, d] thi ophen-4-am i ne

8- ( t r i me t hy 1 s i 1 y 1 ) d i benzo [ b , d ] t h i ophen-2-am i ne 5.43 g (20.0 隱 oi)을 사용하는 것을 제외하고는 준비예 44의 <단계 3>과 동일한 과정을 수행하여 IC-45a-l 2.07 g (7.00瞧 ol, yield ： 35%)과 IC-45b-l 1.95 g (6.60 mmol, yield ： 33%)을 얻었다. <Step 3> of Preparation Example 44, except that 5.43 g (20.0 隱 oi) of 8- (tri me t hy 1 si 1 y 1) di benzo [b, d] thi ophen-2-am i ne 2.07 g (7.00 瞧 ol, yield: 35%) of IC-45a-l and 1.95 g (6.60 mmol, yield: 33%) of IC-45b-l were obtained by the same procedure as described above.

IC-45a— 1의 ¾-NMR ： δ 0.26 (s, 9H) , 6.45 (d, 1Η) , 7.27 (d, 1H)， 7.56 (d, 1H), 7.82 (m, 2H), 8.02 (m, 2H), 8.65 (s, 1H)  ¾-NMR of IC-45a-1: δ 0.26 (s, 9H), 6.45 (d, 1Η), 7.27 (d, 1H), 7.56 (d, 1H), 7.82 (m, 2H), 8.02 (m, 2H), 8.65 (s, 1H)

IC-45b-l의 -應 R ： δ 0.26 (s, 9H), 6.44 (d, 1H) , 7.29 (m, 2H) , 7.53 (d, -應 R of IC-45b-l: δ 0.26 (s, 9H), 6.44 (d, 1H), 7.29 (m, 2H), 7.53 (d,

1H), 8.01 (m, 3H), 8.65 (s, 1H) 1H), 8.01 (m, 3H), 8.65 (s, 1H)

<단계 4> IC-45a의 합성  Step 4 Synthesis of IC-45a

Figure imgf000203_0002
질소 기류 하에서 1.95 g (6.6誦 ol)의 IC-45a-l을 CHC13 I AcOH (40 ml I 40 ml) 에 녹인 후， 0°C에서 NBS 1.19 g (6.6 mmol) 을 천천히 넣고， 상온에서 1시간 교반하였다. 반웅 종결 후 5% NaHC03 수용액에 반웅물을 붓고， 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 목적 화합물인 IC-45a 1.72 g (5.68 mmol, yield ： 86%)을 얻었다.
Figure imgf000203_0002
Dissolve 1.95 g (6.6 μl) of IC-45a-l in CHC1 3 I AcOH (40 ml I 40 ml) under nitrogen stream, slowly add 1.19 g (6.6 mmol) of NBS at 0 ° C, and add 1 ° C at room temperature. Stirred for time. After termination banung banung poured into water to 5% NaHC0 3 aqueous solution, extracted with methylene chloride, which was put into the filter MgS0 4. After removing the solvent of the filtered organic layer By column chromatography, 1.72 g (5.68 mmol, yield: 86%) of the target compound, IC-45a, was obtained.

¾-NMR ： δ 6.44 (d, 1H), 7.28 (t, 1H), 7.42 (d, 1H) , 7.83 (m, 4H), 8.63 ¾-NMR: δ 6.44 (d, 1H), 7.28 (t, 1H), 7.42 (d, 1H), 7.83 (m, 4H), 8.63

(s, 1H) (s, 1H)

<단계 5> IC-45b의 합성  Step 5 Synthesis of IC-45b

Figure imgf000204_0001
Figure imgf000204_0001

IC-45a-l 대신 IC-45b-l 1.95 g (6.60 麵 ol)을 사용하는 것을 제외하고는 준비예 45의 <단계 4>와동일한 과정을 수행하여 IC-45b 1.76 g (5.81 mmol, yield ： 88%)을 얻었다.Except for using IC-45b-l 1.95 g (6.60 麵 ol) instead of IC-45a-l, the same procedure as in <Step 4> of Preparation 45 was carried out to obtain 1.76 g (5.81 mmol, yield) of IC-45b. : 88%).

-匪 R ： δ 6.45 (d, 1H), 7.30 (m, 2H) , 7.45 (d, 1H) , 7.92 (m, 3H) , 8.61 -匪 R: δ 6.45 (d, 1H), 7.30 (m, 2H), 7.45 (d, 1H), 7.92 (m, 3H), 8.61

(s, 1H) (s, 1H)

[준비예 46] IC-46의 합성  Preparation 46 Synthesis of IC-46

<단계 1> 2-(benzof uran一 5_yl )-4,4,5, 5-tetramethyl-l , 3 , 2—di oxabon)lane의  <Step 1> 2- (benzof uran 一 5_yl) -4,4,5, 5-tetramethyl-l, 3, 2—di oxabon) lane

Figure imgf000204_0002
Figure imgf000204_0002

질소 기류 하에서 5-bromobenzofuran (25 g, 0.126 mol), 4,4,4' ,4' ,5,5, 5-bromobenzofuran (25 g, 0.126 mol), 4,4,4 ', 4', 5,5, under nitrogen stream

5 ' , 5 ' -octamethyl-2 , 2 ' -bi ( 1 , 3 , 2-di oxaborolane) (38.67 g, 0.152 mol), Pd(dppf)Cl2 (3.11 g, 3 mol%), KOAc (37.36 g, 0.381 mol) 및 1,4-dioxane (500 ml)를 혼합하고 130°C에서 12시간동안 교반하였다. 5 ', 5' -octamethyl-2, 2 '-bi (1, 3, 2-di oxaborolane) (38.67 g, 0.152 mol), Pd (dppf) Cl 2 (3.11 g, 3 mol%), KOAc (37.36 g, 0.381 mol) and 1,4-dioxane (500 ml) were mixed and stirred at 130 ° C. for 12 hours.

반응이 종결된 후 에틸아세테이트로 추출한 다음 MgS04로 수분을 제거하고, 컬럼크로마토그래피 (Hexane:EA = 10： 1 (v/v))로 정제하여 2- ( benzo f ur an-5-y l)-4,4,5,5-tetr ame t hy 1 - 1 , 3 , 2-d i oxabor o 1 ane (23.23 g, 수율 75%)을 얻었다.After the reaction was completed, the resultant was extracted with ethyl acetate, followed by removing water with MgS0 4 , and purified by column chromatography (Hexane: EA = 10: 1 (v / v)) to obtain 2- (benzofur an-5-yl). -4,4,5,5-tetr ame t hy 1-1, 3, 2-di oxabor o 1 ane (23.23 g, yield 75%) were obtained.

-丽 R: δ 1.25 (s, 12H), 6.46 (d, 1H)， 7.28 (d, 1H) , 7.43 (d, 1H) , 7.53 (d, 1H), 7.98 (s, 1H)  -R R: δ 1.25 (s, 12H), 6.46 (d, 1H), 7.28 (d, 1H), 7.43 (d, 1H), 7.53 (d, 1H), 7.98 (s, 1H)

<단계 2> 5-(2-nitrophenyl)-lH-indole의 합성  <Step 2> Synthesis of 5- (2-nitrophenyl) -lH-indole

Figure imgf000205_0001
Figure imgf000205_0001

질소 기류 하에서 1-brom으 2— nitrobenzene (15.86 g, 78.52 mmol)과 상기 <단계 1>에서 얻은 2-(benzoiuran-5-yl)-4,4,5,5— tetramethyl-l,3,2-dioxaborolane (23 g, 94.23 mmol), K2C03 (32.56g, 235.57 mmol)및 l,4-dioxane/H20(400 ml/200 ml)를 흔합한 다음, 40°C에서 Pd(PPh3)4(4.54 g, 5 mol%)를 넣고 110°C에서 12시간 동안 교반하였다. 2-nitrobenzene (15.86 g, 78.52 mmol) as 1-brom under nitrogen stream and 2- (benzoiuran-5-yl) -4,4,5,5—tetramethyl-l, 3,2 obtained in <Step 1> -dioxaborolane (23 g, 94.23 mmol), K 2 C0 3 (32.56 g, 235.57 mmol) and l, 4-dioxane / H 2 0 (400 ml / 200 ml) were combined and then Pd (PPh) at 40 ° C. 3 ) 4 (4.54 g, 5 mol%) was added and stirred at 110 ° C. for 12 hours.

반응 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 여과하였다. 얻어진 유기층에서 용매를 제거한 후 컬럼 크로마토그래피 (Hexane:EA = 3:1 (v/v))로 정제하여 5-(2-ni trophenyl )benzof uran (12.40 g, 수율 66%)을 얻었다.After completion of the reaction, the mixture was extracted with methylene chloride and MgS0 4 was added and filtered. The solvent was removed from the organic layer and purified by column chromatography (Hexane: EA = 3: 1 (v / v)) to obtain 5- (2-ni trophenyl) benzof uran (12.40 g, yield 66%).

-匿： δ 6.45 (d, 110， 7.26 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.66 (t, 1H), 7.85 (t, 1H), 7.96 (s, 1H) , 8.01 (d, 1H), 8.06 (t, 1H) <단계 3> IC-46의 합성 -匿 δ 6.45 (d, 110, 7.26 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.66 (t, 1H), 7.85 (t, 1H), 7.96 (s, 1H ), 8.01 (d, 1H), 8.06 (t, 1H) Step 3 Synthesis of IC-46

Figure imgf000206_0001
Figure imgf000206_0001

질소 기류 하에서 상기 <단계 2>에서 얻은 5-(2-nitrophenyl)benzofuran (10 g, 41.80 mmol) , t r i pheny 1 hosph i ne (27.41 g, 104.50 mmol)및 1 , 2-d i ch 1 or obenzene (150 ml)를흔합하고 12시간동안교반하였다.  5- (2-nitrophenyl) benzofuran (10 g, 41.80 mmol), tri pheny 1 hosph i ne (27.41 g, 104.50 mmol) and 1, 2-di ch 1 or obenzene obtained in <Step 2> under a nitrogen stream. 150 ml) and stirred for 12 hours.

반웅 종료 후 1， 2-d ich lor obenzene를 제거하고 디클로로메탄으로 추출하였다. 얻어진 유기층에 대해 MgS04로 물을 제거하고, 컬럼크로마토그래피 (Hexane:MC=3:l (v/v))로 정제하여 IC-46 (4.76 g, 수율 55%)올 얻었다.After the reaction, 1, 2-d ich lor obenzene was removed and extracted with dichloromethane. To the obtained organic layer, water was removed with MgSO 4, and purified by column chromatography (Hexane: MC = 3: l (v / v)) to obtain IC-46 (4.76 g, 55% yield).

-NMR: δ 6.51 (d, 1H), 7.27 (d, 1H) , 7.43 (d, 1H), 7.54 (d, 1H), 7.68 (t, 1H), 7.86 (t, 1H), 8.00 (d, 1H), 8.05 (t, 1H), 10.58 (s, 1H)  -NMR: δ 6.51 (d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.54 (d, 1H), 7.68 (t, 1H), 7.86 (t, 1H), 8.00 (d, 1H), 8.05 (t, 1H), 10.58 (s, 1H)

[준비예 47] IC-47의 합성  Preparation 47 Synthesis of IC-47

<단계 1> 2-(benzofuran-6-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane-≤] 합성  Step 1 Synthesis of 2- (benzofuran-6-yl) -4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-≤

Figure imgf000206_0002
Figure imgf000206_0002

5-bromobenzofuran 대신 6—bromobenzofuran을 사용하는 것을 제외하고 준비예 46의 <단계 1>과 동일한 과정을 수행하여 -(benzofuran-6-yl )-4 ,4,5, 5ᅳ tet ramethylᅳ 1 , 3 , 2-d i oxabor o 1 ane-ir 얻었다 .  Except for using 6-bromobenzofuran instead of 5-bromobenzofuran, the same procedure as in <Step 1> of Preparation Example 46 was carried out to obtain-(benzofuran-6-yl) -4, 4,5, 5 ᅳ tet ramethyl ᅳ 1, 3 , 2-di oxabor o 1 ane-ir was obtained.

¾-NMR: 6 1.25 (s, 12H), 6.46 (d, 1H), 7.28 (d, 1H), 7.43 (d, 1H) , 7.53 (d, 1H), 7.98 (s, 1H) ¾-NMR: 6 1.25 (s, 12H), 6.46 (d, 1H), 7.28 (d, 1H), 7.43 (d, 1H), 7.53 (d, 1 H), 7.98 (s, 1 H)

<단계 2> 6-(2-nitrophenyl)benzofuran의 합성  Step 2 Synthesis of 6- (2-nitrophenyl) benzofuran

Figure imgf000207_0001
Figure imgf000207_0001

2-(benzofuran-5-yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (23 g, 94.23 mmol ) 대신 2-(benzofuran-6-yl )-4,4,5,5-tetramethyl-l,3,2-dioxaborolane-i: 사용하는 것을 제외하고는 상기 준비예 46의 <단계 2>와 동일한 과정을 수행하여 6-(2-nitr opheny 1 ) benzof ur an을 얻었다 . 2- (benzofuran-6-yl) -4,4,5 instead of 2- (benzofuran-5-yl) -4,4,5,5-tetramethyl-l, 3,2-dioxaborolane (23 g, 94.23 mmol) , 5-tetramethyl-l, 3,2-dioxaborolane-i: Except for using the same procedure as in <Step 2> of Preparation Example 46 to give 6- (2-nitr opheny 1) benzof ur an .

-NMR: δ 6.45 (d, 1H), 7.26 (d, 1H)， 7.42 (d, 1H), 7.52 (d, 1H) , 7.66 (t, 1H), 7.85 (t, 1H), 7.96 (s, 1H), 8.01 (d, 1H), 8.06 (t, 1H)  -NMR: δ 6.45 (d, 1H), 7.26 (d, 1H), 7.42 (d, 1H), 7.52 (d, 1H), 7.66 (t, 1H), 7.85 (t, 1H), 7.96 (s, 1H), 8.01 (d, 1H), 8.06 (t, 1H)

<단계 3> IC-47의 합성

Figure imgf000207_0002
Step 3 Synthesis of IC-47
Figure imgf000207_0002

5-(2-ni trophenyl )benzofuran 대신 6一 (2— ni trophenyl )benzofuran을 사용하는 것을 제외하고는 상기 준비예 46의 <단계 3〉과 동일한 과정을 수행하여 IC-47를 얻었다. IC-47 was obtained by the same procedure as in <Step 3> of Preparation Example 46 except for using 6- (2-nitrophenyl) benzofuran instead of 5- (2-ni trophenyl) benzofuran.

-NMR: δ 6.51 (d, 1H), 7.27 (d, 1H) , 7.43 (d, 1H)， 7.54 (d, 1H) , 7.68 (t, 1H), 7.86 (t, 1H), 8.00 (d, 1H), 8.05 (t, 1H), 10.58 (s, 1H)  -NMR: δ 6.51 (d, 1H), 7.27 (d, 1H), 7.43 (d, 1H), 7.54 (d, 1H), 7.68 (t, 1H), 7.86 (t, 1H), 8.00 (d, 1H), 8.05 (t, 1H), 10.58 (s, 1H)

[준비예 48] IC-48의 합성  Preparation Example 48 Synthesis of IC-48

<단계 1> dibenz이; b,d]furan-3-amine의 합성

Figure imgf000208_0001
<Step 1>dibenz; b, d] furan-3-amine synthesis
Figure imgf000208_0001

질소 기류 하에서 3-bromodibenzo[b,d]furan (7.41 g, 30.0 mmol)을 THF 100 ml 에 녹인 후， 28 % aqueous a画 onia (10.2 ml, 150麵 ol )과 Cu (0.10 g, 5 mol%)를 넣고， 110°C에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피 ( Hex ane:EA= 10:1 (v/v))로 정제하여 d i benzo [b , d] f ur an-3-am i ne 4.45 g (yield ： 81%)을 얻었다. 3-bromodibenzo [b, d] furan (7.41 g, 30.0 mmol) was dissolved in 100 ml of THF under nitrogen stream, followed by 28% aqueous a aqueousonia (10.2 ml, 150 麵 ol) and Cu (0.10 g, 5 mol%). ) Was added and stirred at 110 ° C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgS0 4 was added, and the mixture was filtered. The solvent of the filtered organic layer was removed, and then purified by column chromatography (Hex ane: EA = 10: 1 (v / v)) to give di benzo [b, d] f ur an-3-am i ne 4.45 g (yield ： 81%).

一圈 R: δ 5.32 (s, 2H), 6.33 (d, 1H), 7.34 (m, 2H)， 7.43 (s, 1H) , 7.65 (d, 2H), 7.89 (dᅳ 1H)  一圈 R: δ 5.32 (s, 2H), 6.33 (d, 1H), 7.34 (m, 2H), 7.43 (s, 1H), 7.65 (d, 2H), 7.89 (d ᅳ 1H)

<단계 2> IC-48의 합성

Figure imgf000208_0002
<Step 2> Synthesis of IC-48
Figure imgf000208_0002

질소 기류 하에서 dibenzo[b,d]furan-3-amine (4.45 g, 24.29 mmol)을 H20/dioxane (10 ml I 90 ml)에 녹인 후， triethanol ammonium chloride (0.45 g, 2.43 mmol)과 RuCl3 H20 (0.055 g, 0.2 mmol)과 PPh3 (0.191 g, 0.7 mmol), SnCl2-2H20 ( 0.548 g, 2.43 mmol)을 넣고， 180°C에서 20시간동안교반하였다. 반응 종결 후 aqueous 5% HC1 에 반응물을 붓고， 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피 (Hexane:MC=l:l (v/v))로 정제하여 IC-48 2.7 g (yield ： 53%)을 얻었다. Dibenzo [b, d] furan-3-amine (4.45 g, 24.29 mmol) was dissolved in H 2 0 / dioxane (10 ml I 90 ml) under nitrogen stream, followed by triethanol ammonium chloride (0.45 g, 2.43 mmol) and RuCl. 3 H 2 0 (0.055 g, 0.2 mmol), PPh 3 (0.191 g, 0.7 mmol), SnCl 2 -2H 2 0 (0.548 g, 2.43 mmol) were added thereto, and the mixture was stirred at 180 ° C. for 20 hours. After completion of the reaction, the reaction mixture was poured into aqueous 5% HC1, extracted with methylene chloride, and filtered with MgS0 4 . After removing the solvent of the filtered organic layer was purified by column chromatography (Hexane: MC = l: l (v / v)) to give 2.7 g (yield: 53%) of IC-48.

H-NMR: δ 6.45 (d, 1H), 7.13 (d, 1H), 7.27 (d, 1H), 7.35 (m, 2H), 7.66 (d H-NMR: δ 6.45 (d, 1H), 7.13 (d, 1H), 7.27 (d, 1H), 7.35 (m, 2H), 7.66 (d

1H), 7.88 (d, 2H), 10.46 (s, 1H) [준비예 49] IC-49의 합성 1H), 7.88 (d, 2H), 10.46 (s, 1H) Preparation 49 Synthesis of IC-49

<단계 1> 5,5-dimethyl-5H-dibenzo[b,d]silol-3-amine 의 합성

Figure imgf000209_0001
<Step 1> Synthesis of 5,5-dimethyl-5H-dibenzo [b, d] silol-3-amine
Figure imgf000209_0001

3-broraod i benzo [b,d]furan 대신 3ᅳ bran으 5 ,5-dimethyl -5H-d i benzo [b,d] silole올 사용하는 것을 제외하고는 상기 준비예 48의 <단계 1>과 동일한 과정올 수행하여 5，5— diniethyI-5H-dibenz이: b,d]silo卜 3ᅳ amine을 얻었다. The same procedure as in <Step 1> of Preparation Example 48 except that 3, bran 5,5-dimethyl-5H-di benzo [b, d] siloleol was used instead of 3-broraod i benzo [b, d] furan. The procedure was followed to obtain 5，5—diniethyI-5H-dibenz: b, d] silo 卜 3 ᅳ amine.

-醒 R: δ 0.68 (s, 6Η), 5.31 (s, 2H)， 6.68 (d, 1H)， 6.80 (sᅳ 1H), 7.33 (t, 1H), 7.52 (d, 1H), 7.61 (t, 1H), 7.64 ,(d, 1H), 7.91 (d, 1H)  -醒 R: δ 0.68 (s, 6Η), 5.31 (s, 2H), 6.68 (d, 1H), 6.80 (s ᅳ 1H), 7.33 (t, 1H), 7.52 (d, 1H), 7.61 (t , 1H), 7.64, (d, 1H), 7.91 (d, 1H)

<단계 2> IC-49의 합성

Figure imgf000209_0002
<Step 2> Synthesis of IC-49
Figure imgf000209_0002

dibenzo[b,d]furan-3-amine 대신 상기 <단계 1>에서 얻은 5,5-dimethyl-5H-dibenzo[b,d]silol-3-amine을 사용하는 것을 제외하고는 상기 준비예 48의 <단계 2>과 동일한 과정을 수행하여 IC-49을 얻었다.  Except for using 5,5-dimethyl-5H-dibenzo [b, d] silol-3-amine obtained in <Step 1> instead of dibenzo [b, d] furan-3-amine. IC-49 was obtained by the same procedure as in <Step 2>.

ᅳ匪 R: 50.66 (s, 6H), 6.45 (d, 1H) , 7.27 (d, 1H), 7.33 (t, 1H) , 7.52 (d, 1H), 7.61 (t, 1H)„ 7.79 (d, 1H), 7.89 (d, 1H), 7.97 (d, 1H), 10.42 (s, 1H)  ᅳ 匪 R: 50.66 (s, 6H), 6.45 (d, 1H), 7.27 (d, 1H), 7.33 (t, 1H), 7.52 (d, 1H), 7.61 (t, 1H) „7.79 (d, 1H), 7.89 (d, 1H), 7.97 (d, 1H), 10.42 (s, 1H)

[준비예 50] IC-50의 합성  Preparation 50 Synthesis of IC-50

<단계 1> 5,5-diphenyl-5H-dibenzo[b,d]si lol-3-amine의 합성

Figure imgf000210_0001
Step 1 Synthesis of 5,5-diphenyl-5H-dibenzo [b, d] si lol-3-amine
Figure imgf000210_0001

3 bromod i benzo [b,d] fur an 대신 3-bromo-5 , 5-d i pheny 1 -5H-d i benzo [b , d ] silole을 사용하는 것을 제외하고는 상기 준비예 48의 <단계 1>과 동일한 과정을 수행하여 5,5-diphenyl-5H-dibenzo[b,d]silo卜 3ᅳ amine을 얻었다. Except for using 3-bromo-5, 5-dipheny 1-5H-di benzo [b, d] silole instead of 3 bromod i benzo [b, d] fur an <Step 1> 5,5-diphenyl-5H-dibenzo [b, d] silo 卜 3 ᅳ amine was obtained by the same procedure as described above.

-匪 R: δ 5.33 (s, 2Η), 6.67 (d, 1H) , 6.81 (s, 1Η)， 7.31 (t, 1H)， 7.37 (m, 4H), 7.46 (m, 4H), 7.54 (m, 3H), 7.62 (t, 1H), 7.66 (d, 1H) ' 7.92 (d, 1H)  -匪 R: δ 5.33 (s, 2Η), 6.67 (d, 1H), 6.81 (s, 1Η), 7.31 (t, 1H), 7.37 (m, 4H), 7.46 (m, 4H), 7.54 (m , 3H), 7.62 (t, 1H), 7.66 (d, 1H) '7.92 (d, 1H)

<단계 2> IC-50의 합성  <Step 2> Synthesis of IC-50

Figure imgf000210_0002
Figure imgf000210_0002

dibenzo[b,d]furanᅳ 3ᅳ amine 대신 <단계 1>에서  instead of dibenzo [b, d] furan ᅳ 3 ᅳ amine,

5,5-diphenyl-5H-dibenzo[b,d]silol-3-amine을 사용하는 것을 제외하고는 상기 준비예 48의 <단계 2>과동일한과정을 수행하여 IC-50을 얻었다.Except for using 5,5-diphenyl-5H-dibenzo [b, d] silol-3-amine was carried out the same procedure as in <Step 2> of Preparation Example 48 to obtain an IC-50.

-刚 R: δ 6.44 (d, 1H), 7.26 (d, 1H) , 7.35 (m, 5H) , 7.47 (m, 4H), 7.53 (m, 3H), 7.62 (t, 1H), 7.78 (d, 1H), 7.90 (d, 1H), 7.96 (d, 1H), 10.41 (s, 1H)  -刚 R: δ 6.44 (d, 1H), 7.26 (d, 1H), 7.35 (m, 5H), 7.47 (m, 4H), 7.53 (m, 3H), 7.62 (t, 1H), 7.78 (d , 1H), 7.90 (d, 1H), 7.96 (d, 1H), 10.41 (s, 1H)

[준비예 51] IC-51의 합성  Preparation Example 51 Synthesis of IC-51

<단계 1> IC-51의 합성

Figure imgf000210_0003
<Step 1> Synthesis of IC-51
Figure imgf000210_0003

dibenzo[b,d]furan-3-amine 대신 dibenzo[b,d]selenophenᅳ 3ᅳ amine을 사용하는 것올 제외하고는 상기 준비예 48의 <단계 2〉과 동일한 과정을 수행하여 IC-51을 얻었다.dibenzo [b, d] selenophenan3 ᅳ amine instead of dibenzo [b, d] furan-3-amine Except for using the same procedure as in <Step 2> of Preparation Example 48 to obtain an IC-51.

-丽 R: δ 6.47 (d, 1Η)' 7.15 (d, 1H), 7.26 (d, 1H), 7.36 (m, 2H) , 7.67 (d, 1H), 7.89 (d, 2H), 10.45 (s, 1H)  -丽 R: δ 6.47 (d, 1Η) '7.15 (d, 1H), 7.26 (d, 1H), 7.36 (m, 2H), 7.67 (d, 1H), 7.89 (d, 2H), 10.45 (s , 1H)

[준비예 52] IC-52의 합성 Preparation Example 52 Synthesis of IC-52

Figure imgf000211_0001
Figure imgf000211_0001

2- ( benzo [b ] se 1 enophen-5-y 1 )-4,4,5, 5~t et r amethy 1 -1 , 3 , 2-di oxabor plane 합성 Synthesis of 2- (benzo [b] se 1 enophen-5-y 1) -4,4,5,5 ~ t et r amethy 1 -1, 3, 2-di oxabor plane

Figure imgf000211_0002
Figure imgf000211_0002

5-bromobenzofuran 대신 5— br omobenzo [b]sel enophene을 사용하는 것을 제외하고는 상기 준비예 46의 <단계 1>과 동일한 과정을 수행하여 2- ( benzo [ b ] s e 1 enophen-5-y 1 )-4,4,5,5-tetramethyl-l,3,2-dioxaborolane-ir" 얻었다 . Except for using 5— bromobenzo [b] sel enophene instead of 5-bromobenzofuran, the same procedure as in <Step 1> of Preparation Example 46 was performed to obtain 2- (benzo [b] se 1 enophen-5-y 1 ), 4,4,5,5-tetramethyl-l, 3,2-dioxaborolane-ir " .

¾ᅳ删 R: δ 1.26 (s, 12H), 6.45 (d, 1H) , 7.27 (d, 1H)ᅳ 7.43 (d, 1H), 7.54 (d, 1H), 8.00 (s, 1H)  ¾ ᅳ 删 R: δ 1.26 (s, 12H), 6.45 (d, 1H), 7.27 (d, 1H) ᅳ 7.43 (d, 1H), 7.54 (d, 1H), 8.00 (s, 1H)

<단계 2> 5— (2— nitrophenyl)benzo[b]selenophene의 합성  Step 2 Synthesis of 5— (2—nitrophenyl) benzo [b] selenophene

Figure imgf000211_0003
Figure imgf000211_0003

2ᅳ (benzo fur anᅳ 5ᅳ yl )-4,4,5, 5-tetramethyl-l , 3， 2-dioxaborol ane 대신 - ( benzo [b ] se 1 enophen-5-y 1 )-4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborol ane-i: 2 ᅳ (benzo fur an ᅳ 5 ᅳ yl) -4,4,5, 5-tetramethyl-l, 3, instead of 2-dioxaborol ane-(benzo [b] se 1 enophen-5-y 1) -4, 4 , 5, 5-tetramethyl-l, 3, 2-dioxaborol ane-i:

β)o)O)()υ( SHznp0HAKpKIp L L S S9卜Ip.. *, - -. -- - - - o)( 3)))Ho8p 88ns s†I s -- " -· -ᅳ - β ) o) O ) () υ ( SHznp0HAKpKIp LLS S9 卜 Ip .. * ,--.----o ) ( 3 ))) Ho8 p 88ns s † I s- " -----

Οΐ Οΐ

Figure imgf000212_0001
Figure imgf000212_0001

IS} IS}

22

Γ,,,,,,, ( () () ) ())st.dHHHH 1H 101 10111 Γ, ,, ,,,, (( ) ()) ()) s t. d HHHH 1H 10 1 101 11

,,,,,,,,, () ( () () ()ddd.5dH.tMR δ.H 7.H 7.3H 71767 ¾N 6521271412:— 0 1 ,,,,,, ,,, ( ) (() () () ddd.5dH t MR δ.H 7.H 7.3H 71767 ¾N 652127 1 4 1 2: -. 0 1

Figure imgf000213_0001
Figure imgf000213_0001

,, ,,,,,,)) () ( () (sdd.dH 7.57 HNMR δ.1H.H 7.81H 741T242651244: [합성예 111] 1치11의 합성 ,,,, ,,,,)) () (() (sdd.dH 7.57 HNMR δ.1H.H 7.81H 741T242651244: Synthesis Example 111 Synthesis of Value 11

Figure imgf000214_0001
Figure imgf000214_0001

IC-la 대신 준비예 32에서 제조한 IC-32 사용하고 Instead of IC-la, use IC-32 prepared in Preparation Example 32

2-br omo-4 , 6-d i pheny 1 pyr i d i ne 대신 2一 bromoᅳ 4,6一 diphenylpyr idine을사용하는 것을 제외하고는 합성예 1과 동일한 과정올 수행하여 목적 화합물인 Inv-lll(3.89 g, 수율 64%)를 얻었다. Inv-lll (3.89) was carried out in the same manner as in Synthesis Example 1, except that 2-bromo 4,6-diphenylpyr idine was used instead of 2-br omo-4 and 6-di pheny 1 pyr idi ne. g, yield 64%).

GC-Mass (이론치： 452.13 g/mol , 측정치: 452 g/mol)  GC-Mass (Theoretical value: 452.13 g / mol, Measured value: 452 g / mol)

[합성예 112] Inv-112의 합성  Synthesis Example 112 Synthesis of Inv-112

Figure imgf000214_0002
Figure imgf000214_0002

IC-la 대신 준비예 32에서 제조한 IC-32a을 사용하고 2-br omo-4, 6-d i phenyl pyridine 대신 4-bromo-2— (pyridin— 3— yl)pyrimidine을 사용하는 것을 제외하고 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-112(3 g, 수율 59%) 얻었다.  Synthesis except using IC-32a prepared in Preparation Example 32 instead of IC-la and 4-bromo-2— (pyridin— 3—yl) pyrimidine instead of 2-br omo-4, 6-di phenyl pyridine Inv-112 (3 g, 59% yield) of the target compound was obtained by the same procedure as in Example 1.

GC-Mass (이론치: 378.09 g/mol, 측정치: 378 g/mol)  GC-Mass (Theoretical value: 378.09 g / mol, Measured value: 378 g / mol)

[합성예 113] Inv-113의 합성 Synthesis Example 113 Synthesis of Inv-113

Figure imgf000215_0001
Figure imgf000215_0001

IC-la 대신 준비예 33에서 제조한 IC-33을 사용하고 2-br omo-4 , 6~d i heny 1 py r i d i ne 대신 l-bromo-4-phenyl isoqui ol ine^-사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-113(3.26 g, 수율 58%)를 얻었다.  Except for using IC-33 prepared in Preparation Example 33 instead of IC-la and l-bromo-4-phenyl isoqui ol ine ^-instead of 2-br omo-4, 6 ~ di heny 1 py ridi ne Inv-113 (3.26 g, yield 58%) was obtained by the same procedure as in Synthesis Example 1.

GC-Mass (이론치: 436.19 g/mol, 측정치: 436 g/mol)  GC-Mass (Theoretical value: 436.19 g / mol, Measured value: 436 g / mol)

[합성예 114] Inv-114의 합성  Synthesis Example 114 Synthesis of Inv-114

Figure imgf000215_0002
Figure imgf000215_0002

IC-la 대신 준비예 34에서 제조한 IC-34를 사용하고 2-br omo-4 , 6-d i pheny 1 pyr idine 대신 4ᅳ bromoᅳ 2, 6ᅳ diphenylpyr idine을사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Inv-114(3.11 g, 수율 63«를 얻었다.  Synthesis example except for using IC-34 prepared in Preparation Example 34 instead of IC-la and 4 ᅳ bromo ᅳ 2, 6 ᅳ diphenylpyr idine instead of 2-br omo-4, 6-di pheny 1 pyr idine The same procedure as in 1 was carried out to obtain the title compound Inv-114 (3.11 g, yield 63 «.

GC-Mass (이론치 : 586.24 g/mol , 측정치 : 586 g/mol)  GC-Mass (Theoretical value: 586.24 g / mol, Measured value: 586 g / mol)

[합성예 115] Inv-115의 합성

Figure imgf000216_0001
Synthesis Example 115 Synthesis of Inv-115
Figure imgf000216_0001

lnv-115  lnv-115

질소 기류 하에서 IC-35 (2.23 g, 10.0 mmol), 2-br omo-4 , 6-d i pheny 1 pyr i d i ne (3.72 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) 및 DMF(30 ml)를혼합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후， 컬럼 크로마토그래피로 정제하여 목적 화합물인 lnv-115 (3.85 g, yield ： 85%)를 얻었다.  IC-35 (2.23 g, 10.0 mmol), 2-br omo-4, 6-di pheny 1 pyr idi ne (3.72 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) and DMF (30 ml) under nitrogen stream ) Were mixed and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered, and the residue was purified by column chromatography to obtain lnv-115 (3.85 g, yield: 85%) as a target compound.

. GC-Mass (이론치 : 452.57 g/mol , 측정치 : 452 g/mol) . GC-Mass (Theoretical value: 452.57 g / mol, Measured value: 452 g / mol)

[합성예 116] Inv-116의 합성  Synthesis Example 116 Synthesis of Inv-116

Figure imgf000216_0002
Figure imgf000216_0002

질소 기류 하에서 IC-35 (2.23 g, 10.0 删 ol), IC-35 (2.23 g, 10.0 μl ol) under nitrogen stream,

2-ch 1 or 0-4 , 6-d i pheny 1 - 1 , 3 , 5- 1 r i az i ne (3.21 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) 및 DMF(30 ml)를흔합하고 상온에서 3시간동안교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후， 컬럼 크로마토그래피로 정제하여 목적 화합물인 Inv-116 (3.95 g, yield ： 87%)를 얻었다. Combine 2-ch 1 or 0-4, 6-di pheny 1-1, 3, 5- 1 ri az i ne (3.21 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) and DMF (30 ml) Stir for 3 hours at room temperature. After the reaction was completed, water was added, the solid compound was filtered, and the residue was purified by column chromatography to obtain Inv-116 (3.95 g, yield: 87%) as a target compound.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 117] Inv-117의 합성 Synthesis Example 117 Synthesis of Inv-117

Figure imgf000217_0001
Figure imgf000217_0001

질소 기류 하에서 IC-35 (2.23 g, 10.0 mmol), 2- (3-br omopheny 1 ) -4 , 6-d i phenyl -1 , 3 , 5-t r i az i ne (4.66 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) 및 DMF(30 ml)를 흔합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 Inv-117 (3.40 g, yield ： 64%)를 얻었다.  IC-35 (2.23 g, 10.0 mmol), 2- (3-br omopheny 1) -4, 6-di phenyl -1, 3, 5-tri az i ne (4.66 g, 12.0 mmol), NaH under nitrogen stream (0.29 g, 12.0 mmol) and DMF (30 ml) were combined and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered, and the residue was purified by column chromatography to obtain Inv-117 (3.40 g, yield: 64%) as a target compound.

GC-Mass (이론치 : 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 118] Inv-118의 합성  Synthesis Example 118 Synthesis of Inv-118

Figure imgf000217_0002
Figure imgf000217_0002

lnv-118  lnv-118

IC-35 대신 IC— 36 (2.23 g, 10.0 匪 ol)을 사용하는 것을 제외하고는 합성예 116과 동일한 과정을 수행하여 Inv-118 (3.95 g, yield ： 87%)을 얻었다.  Inv-118 (3.95 g, yield: 87%) was obtained in the same manner as in Synthesis Example 116 except that IC-36 (2.23 g, 10.0 μl ol) was used instead of IC-35.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 119] Inv-119의 합성 Synthesis Example 119 Synthesis of Inv-119

Figure imgf000218_0001
Figure imgf000218_0001

질소 기류 하에서 IC-36 (2.23 g, 10.0 隱 ol), 2- ( 4-br omopheny 1 ) -4 , 6-d i pheny 1 - 1 , 3 , 5- 1 r i az i ne (4.66 g, 12.0 mmol), NaH (0.29 g, 12.0 mmol) 및 DMF(30 ml)를 흔합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후， 컬럼 크로마토그래피로 정제하여 목적 화합물인 Inv-119 (3.61 g, yield ： 68%)를 얻었다.  IC-36 (2.23 g, 10.0 μl ol), 2- (4-br omopheny 1) -4, 6-di pheny 1-1, 3, 5- 1 ri az i ne (4.66 g, 12.0 mmol) under nitrogen stream ), NaH (0.29 g, 12.0 mmol) and DMF (30 ml) were combined and stirred at room temperature for 3 hours. After the reaction was completed, water was added, the solid compound was filtered, and the residue was purified by column chromatography to obtain Inv-119 (3.61 g, yield: 68%) as a target compound.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 120] Inv-120의 합성  Synthesis Example 120 Synthesis of Inv-120

Figure imgf000218_0002
Figure imgf000218_0002

IC-35 대신 IC-36 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 117과동일한과정을수행하여 Inv-120 (3.50 g, yield ： 66%)을 얻었다.  Inv-120 (3.50 g, yield: 66%) was obtained by the same procedure as Synthesis Example 117 except for using IC-36 (2.23 g, 10.0 mmol) instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 121] Inv-121의 합성 Synthesis Example 121 Synthesis of Inv-121

Figure imgf000219_0001
Figure imgf000219_0001

IC-35 대신 IC-37 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 와동일한 과정을 수행하여 Inv-121 (3.67 g, yield ： 8 )을 얻었다.  Inv-121 (3.67 g, yield: 8) was obtained in the same manner as the synthesis example except that IC-37 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치 : 452.57 g/mol, 측정치: 452 g/mol)  GC-Mass (Theoretical value: 452.57 g / mol, Measured value: 452 g / mol)

[합성예 122] Ιην^122의 합성  Synthesis Example 122 Synthesis of Ιην ^ 122

Figure imgf000219_0002
Figure imgf000219_0002

IC-35 대신 IC-37 (2.23 g, 10.0 画 ol)을 사용하는 것올 제외하고는 합성예 과 동일한과정을 수행하여 Inv— 122 (3.73 g, yield ： 82%)을 얻었다.  Exv 122 (3.73 g, yield: 82%) was obtained in the same manner as in Synthesis Example, except that IC-37 (2.23 g, 10.0 μl) was used instead of IC-35.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 123] Inv-123의 합성  Synthesis Example 123 Synthesis of Inv-123

Figure imgf000219_0003
Figure imgf000219_0003

IC-35 대신 IC-37 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을 수행하여 Inv— 123 (3.66 g, yield ： 69%)을 얻었다. Synthesis example except for using IC-37 (2.23 g, 10.0 mmol) instead of IC-35 The same procedure was followed to obtain Inv- 123 (3.66 g, yield: 69%).

GC-Mass (이론치 : 530.64 g/mol , 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 124] Ιην^124의 합성  Synthesis Example 124 Synthesis of Ιην ^ 124

Figure imgf000220_0001
Figure imgf000220_0001

IC-35 대신 IC-38 (2.23 g, 10.0 隱 ol)을 사용하는 것을 제외하고

Figure imgf000220_0002
과 동일한과정을 수행하여 Inv-124 (3.91 g, yield ： 86«을 얻었다. Except for using IC-38 (2.23 g, 10.0 μl ol) instead of IC-35
Figure imgf000220_0002
Inv-124 (3.91 g, yield: 86 «was obtained by the same procedure as in the above.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 125] Inv-125의 합성  Synthesis Example 125 Synthesis of Inv-125

Figure imgf000220_0003
Figure imgf000220_0003

IC-36 대신 IC-38 (2.23 g, 10.0 隱 ol)을 사용하는 것을 제외하고는 합성예 와동일한과정을수행하여 Inv-125 (3.24 g, yield ： 61¾>)을 얻었다.  Inv-125 (3.24 g, yield: 61¾>) was obtained in the same manner as the synthesis example except that IC-38 (2.23 g, 10.0 μl ol) was used instead of IC-36.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 126] Inv-126의 합성 Synthesis Example 126 Synthesis of Inv-126

Figure imgf000221_0001
Figure imgf000221_0001

IC-35 대신 IC-38 (2.23 g, 10.0 mmol)를 사용하는 것올 제외하고는 합성예 과동일한과정을 수행하여 Inv-126 (3.50 g, yield ： 66%)을 얻었다.  Inv-126 (3.50 g, yield: 66%) was obtained by the same procedure as in Synthesis except that IC-38 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치 : 530.64 g/mol, 측정치 : 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 127] Ιην^127의 합성  Synthesis Example 127 Synthesis of Ιην ^ 127

Figure imgf000221_0002
Figure imgf000221_0002

Inv-127  Inv-127

IC-35 대신 IC-39 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 와동일한과정을수행하여 Inv-127 (3.94 g, yield ： 87%)을 얻었다.  Inv-127 (3.94 g, yield: 87%) was obtained in the same manner as the synthesis example except that IC-39 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 452.57 g/mol, 측정치: 452 g/mol)  GC-Mass (Theoretical value: 452.57 g / mol, Measured value: 452 g / mol)

[합성예 128] Inv-128의 합성  Synthesis Example 128 Synthesis of Inv-128

Figure imgf000221_0003
IC-35 대신 IC-39 (2.23 g, 10.0 mmol)을 사용하는 것을쎄외하고는 합성예 과 동일한과정을 수행하여 Inv-128 (3.64 g, yield ： 80%)을 얻었다.
Figure imgf000221_0003
Exv-128 (3.64 g, yield: 80%) was obtained in the same manner as in Synthesis Example, except that IC-39 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치 : 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 129] Inv-129의 합성  Synthesis Example 129 Synthesis of Inv-129

Figure imgf000222_0001
Figure imgf000222_0001

IC-35 대신 IC-39 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Inv-129 (2.44 g, yield ： 46%)을 얻었다.  Inv-129 (2.44 g, yield: 46%) was obtained in the same manner as the synthesis example except that IC-39 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol) ·  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 130] Inv-130의 합성  Synthesis Example 130 Synthesis of Inv-130

Figure imgf000222_0002
Figure imgf000222_0002

IC-35 대신 IC-40 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Ιην-130 (4. 5 g, yield ： 89%)을 얻었다.  Ηη-130 (4.5 g, yield: 89%) was obtained by the same procedure as in Synthesis Example, except that IC-40 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 131] Inv-131의 합성 Synthesis Example 131 Synthesis of Inv-131

Figure imgf000223_0001
Figure imgf000223_0001

IC-36 대신 ICᅳ 40 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 와동일한과정을수행하여 Inv-131 (2.92 g, yield ： 55%)을 얻었다.  Inv-131 (2.92 g, yield: 55%) was obtained in the same manner as the synthesis example except for using IC ᅳ 40 (2.23 g, 10.0 mmol) instead of IC-36.

GC-Mass (이론치 : 530.64 g/mol , 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 132] Im l32의 합성  Synthesis Example 132 Synthesis of Im l32

Figure imgf000223_0002
Figure imgf000223_0002

IC-35 대신 ICᅳ 40 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Inv-132 (3.34 g, yield ： 63%)을 얻었다.  Inv-132 (3.34 g, yield: 63%) was obtained in the same manner as the synthesis example except for using IC ᅳ 40 (2.23 g, 10.0 mmol) instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 133] Inv-133의 합성  Synthesis Example 133 Synthesis of Inv-133

Figure imgf000223_0003
Figure imgf000223_0003

IC-35 대신 IC-41 (2.23 g, 10.0 mmol)을 사용하는 것올 제외하고는 합성예 와동일한 과정을 수행하여 Inv— 133 (3.85 g, yield ： 85%)을 얻었다. Synthesis example except for using IC-41 (2.23 g, 10.0 mmol) instead of IC-35 The same procedure was followed to obtain Inv-133 (3.85 g, yield: 85%).

GC-Mass (이론치 : 452.57 g/mol , 측정치: 452 g/mol)  GC-Mass (Theoretical value: 452.57 g / mol, Measured value: 452 g / mol)

[합성예 134] Inv-134의 합성  Synthesis Example 134 Synthesis of Inv-134

Figure imgf000224_0001
Figure imgf000224_0001

IC-35 대신 IC-41 (2.23 g, 10.0 隱 ol)을 사용하는 것을 제외하고는 합성예 과동일한 과정을수행하여 Inv-134 (3.95 g, yield ： 87%)올 얻었다.  Inv-134 (3.95 g, yield: 87%) was obtained in the same manner as in Synthesis Example, except that IC-41 (2.23 g, 10.0 μl ol) was used instead of IC-35.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 135] Inv-135의 합성  Synthesis Example 135 Synthesis of Inv-135

Figure imgf000224_0002
Figure imgf000224_0002

IC-35 대신 IC-41 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과 동일한과정을수행하여 Inv-135 (3.50 g, yield ： 66%)을 얻었다.  Inv-135 (3.50 g, yield: 66%) was obtained in the same manner as the synthesis example except for using IC-41 (2.23 g, 10.0 mmol) instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 136] Inv-136의 합성

Figure imgf000225_0001
Synthesis Example 136 Synthesis of Inv-136
Figure imgf000225_0001

IC-35 대신 IC-42a (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Inv-136 (4.09 g, yield ： 90%)을 얻었다.  Inv-136 (4.09 g, yield: 90%) was obtained in the same manner as the synthesis example except that IC-42a (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 137] Inv-137의 합성  Synthesis Example 137 Synthesis of Inv-137

Figure imgf000225_0002
Figure imgf000225_0002

IC-36 대신 IC-42a (2.23 g, 10.0 mmol)을사용하는 것을 제외하고는 합성예 와동일한과정을 수행하여 Inv-137 (3.18 g, yield ： 60%)올 얻었다.  Inv-137 (3.18 g, yield: 60%) was obtained in the same manner as the synthesis example except that IC-42a (2.23 g, 10.0 mmol) was used instead of IC-36.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 138] I l38의 합성  Synthesis Example 138 Synthesis of I l38

Figure imgf000225_0003
IC-35 대신 IC-42a (2.23 g, 10.0匪 ol)을사용하는 것을 제외하고는 합성예 과 동일한과정을수행하여 Inv-138 (2.97 g, yield ： 56«을 얻었다.
Figure imgf000225_0003
Inv-138 (2.97 g, yield: 56 «was obtained in the same manner as the synthesis example except that IC-42a (2.23 g, 10.0 μl ol) was used instead of IC-35.

GC-Mass (이론치 : 530.64 g/mol , 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 139] Im l39의 합성  Synthesis Example 139 Synthesis of Im l39

Figure imgf000226_0001
Figure imgf000226_0001

IC-35 대신 IC-42b (2.23 g, 10.0隱 ol)을 사용하는 것을 제외하고는 합성예 와동일한과정을 수행하여 Inv-139 (3.67 g, yield ： 81%)을 얻었다.  Inv-139 (3.67 g, yield: 81%) was obtained by the same procedure as in Synthesis Example, except that IC-42b (2.23 g, 10.0 μl ol) was used instead of IC-35.

GC-Mass (이론치 : 452.57 g/mol , 측정치: 452 g/mol)  GC-Mass (Theoretical value: 452.57 g / mol, Measured value: 452 g / mol)

[합성예 140] Inv-140의 합성  Synthesis Example 140 Synthesis of Inv-140

Figure imgf000226_0002
Figure imgf000226_0002

IC-35 대신 IC-42b (2.23 g, 10.0應 iol)을 사용하는 것올 제외하고는 합성예 과 동일한과정을수행하여 Inv-140 (3.95 g, yield ： 87%)을 얻었다.  Inv-140 (3.95 g, yield: 87%) was obtained in the same manner as the synthesis example except that IC-42b (2.23 g, 10.0 k iol) was used instead of IC-35.

GC-Mass (이론치 : 454.55 g/mol , 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 141] Invl41의 합성 Synthesis Example 141 Synthesis of Invl41

Figure imgf000227_0001
Figure imgf000227_0001

IC-35 대신 IC-42b (2.23 g, 10.0隱 ol)를사용하는 것을 제외하고

Figure imgf000227_0002
과 동일한과정을 수행하여 Inv-141 (3.45 g, yield ： 65%)을 얻었다. Except for using IC-42b (2.23 g, 10.0 隱 ol) instead of IC-35
Figure imgf000227_0002
Inv-141 (3.45 g, yield: 65%) was obtained by the same procedure as in the following procedure.

GC-Mass (이론치: 530.64 g/mol, 측정치 : 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 142] Ιην^142의 합성  Synthesis Example 142 Synthesis of Ιην ^ 142

Figure imgf000227_0003
Figure imgf000227_0003

IC-35 대신 IC_32a (2.23 g, 10.0 mmol)을 사용하는 것올 제외하고는 합성예 과 동일한과정을수행하여 Inv-142 (3.77 g, yield ： 83%)을 얻었다.  Inv-142 (3.77 g, yield: 83%) was obtained in the same manner as the synthesis example except for using IC_32a (2.23 g, 10.0 mmol) instead of IC-35.

GC-Mass (이론치: 454.55 g/mol, 측정치: 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 143] In l 3의 합성  Synthesis Example 143 Synthesis of In l 3

Figure imgf000227_0004
IC-36 대신 IC-32a (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 와동일한과정을수행하여 Inv-143 (3.45 g, yield ： 65%)을 얻었다.
Figure imgf000227_0004
Inv-143 (3.45 g, yield: 65%) was obtained in the same manner as the synthesis example except that IC-32a (2.23 g, 10.0 mmol) was used instead of IC-36.

GC-Mass (이론치 : 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 144] Inv-144의 합성  Synthesis Example 144 Synthesis of Inv-144

Figure imgf000228_0001
Figure imgf000228_0001

IC-35 대신 IC-32a (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Inv-144 (3.77 g, yield ： 71%)을 얻었다.  Inv-144 (3.77 g, yield: 71%) was obtained in the same manner as the synthesis example except that IC-32a (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 145] Invl45의 합성  Synthesis Example 145 Synthesis of Invl45

Figure imgf000228_0002
Figure imgf000228_0002

IC-35 대신 IC— 32b (2.23 g, 10.0誦 ol)을 사용하는 것을 제외하고는 합성예 와동일한과정을수행하여 Inv-145 (3.76 g, yield ： 83%)을 얻었다.  Inv-145 (3.76 g, yield: 83%) was obtained in the same manner as the synthesis example except that IC-32b (2.23 g, 10.0 μl ol) was used instead of IC-35.

GC-Mass (이론치: 452.57 g/mol, 측정치: 452 g/mol)  GC-Mass (Theoretical value: 452.57 g / mol, Measured value: 452 g / mol)

[합성예 146] Inv_146의 합성 Synthesis Example 146 Synthesis of Inv_146

Figure imgf000229_0001
Figure imgf000229_0001

IC-35 대신 IC-32b (2.23 g, 10.0匪 ol)을사용하는 것을 제외하고는 합성예 과 동일한 과정을 수행하여 Inv-146 (3.77 g, yield ： 83%)을 얻었다.  Inv-146 (3.77 g, yield: 83%) was obtained in the same manner as the synthesis example except for using IC-32b (2.23 g, 10.0 μl ol) instead of IC-35.

GC-Mass (이론치 : 454.55 g/mol, 측정치 : 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 147] Inv~147의 합성  Synthesis Example 147 Synthesis of Inv ~ 147

Figure imgf000229_0002
Figure imgf000229_0002

IC-35 대신 IC— 32b (2.23 g, 10.0 mmol)을사용하는 것을 제외하고는 합성예 과 동일한 과정을 수행하여 Inv-147 (3.77 g, yield ： 7 )을 얻었다.  Inv-147 (3.77 g, yield: 7) was obtained in the same manner as the synthesis example except that IC-32b (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 148] Inv-148의 합성  Synthesis Example 148 Synthesis of Inv-148

Figure imgf000229_0003
Figure imgf000229_0003

IC-35 대신 IC-43 (2.23 g, 10.0 mmol)을 사용하는 것올 제외하고는 합성예 과 동일한과정을수행하여 Inv-148 (3.50 g, yield ： 77%)을 얻었다. Synthesis example except for using IC-43 (2.23 g, 10.0 mmol) instead of IC-35 Inv-148 (3.50 g, yield: 77%) was obtained by the same procedure as in.

GC-Mass (이론치 : 454.55 g/mol , 측정치 : 454 g/mol)  GC-Mass (Theoretical value: 454.55 g / mol, Measured value: 454 g / mol)

[합성예 149] Inv-149의 합성  Synthesis Example 149 Synthesis of Inv-149

Figure imgf000230_0001
Figure imgf000230_0001

IC-36 대신 IC-43 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 와 동일한과정을 수행하여 Inv-149 (3.08 g, yield ： 58%)을 얻었다.  Inv-149 (3.08 g, yield: 58%) was obtained in the same manner as the synthesis example except for using IC-43 (2.23 g, 10.0 mmol) instead of IC-36.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 150] Inv-150의 합성  Synthesis Example 150 Synthesis of Inv-150

Figure imgf000230_0002
Figure imgf000230_0002

IC-35 대신 IC-43 (2.23 g, 10.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Inv-150 (4.14 g, yield ： 78%)을 얻었다.  Inv-150 (4.14 g, yield: 78%) was obtained by the same procedure as the synthesis example except that IC-43 (2.23 g, 10.0 mmol) was used instead of IC-35.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 151] I 151의 합성 Synthesis Example 151 Synthesis of I 151

Figure imgf000231_0001
Figure imgf000231_0001

lnv-151 질소 기류 하에서 2.42 g (8.0 mmol)의 IC— 44， 1.07g (8.8 麵 ol)의 phenylboronic acid, 0.96 g (24.0 画 ol)의 NaOH과 40 ml/20 ml의 THF/H20를 넣고 교반하였다. 40°C에서 0.46 g (5 mol%)의 Pd(PPh3)4를 넣고 80°C에서 12시간 동안 교반하였다. 반응 종결 후 메틸렌클로라이드로 추출하고 MgS04를 넣고 필터하였다. 필터된 유기층의 용매를 제거한 후 컬럼크로마토그래피를 이용하여 상기 중간 화합물인 Ιην-151-l 2.06 g (yield: 86 %)을 획득하였다. 2.42 g (8.0 mmol) of IC—44, 1.07 g (8.8 μl) of phenylboronic acid, 0.96 g (24.0 μl) of NaOH and 40 ml / 20 ml of THF / H 2 O under a stream of lnv-151 nitrogen Put and stir. At 40 ° C into a Pd (PPh 3) 4 of 0.46 g (5 mol%) was stirred at 80 ° C for 12 hours. After completion of the reaction, the mixture was extracted with methylene chloride, MgS0 4 was added, and the mixture was filtered. After removing the solvent of the filtered organic layer using column chromatography to obtain 2.06 g (yield: 86%) of the intermediate compound Ιην-151-l.

질소 기류 하에서 상기 중간 화합물인 Ιην-151-l (2.06 g, 6.88 睡 ol), 2-chl or 0-4 , 6-d i phenyl -1 , 3 , 5-t r i az i ne (2.21 g, 8.26瞧 ol), NaH (1.98 g, 8.26 mmol) 및 DMF(40 ml)를 흔합하고 상온에서 3시간동안교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 lnv-151 (3.10 g, 수율 85%)를 얻었다.  Ιην-151-l (2.06 g, 6.88 睡 ol), 2-chl or 0-4, 6-di phenyl -1, 3, 5-tri az i ne (2.21 g, 8.26 瞧) under nitrogen stream ol), NaH (1.98 g, 8.26 mmol) and DMF (40 ml) were combined and stirred for 3 hours at room temperature. After the reaction was completed, water was added, the solid compound was filtered, and the residue was purified by column chromatography to obtain lnv-151 (3.10 g, yield 85%) as a target compound.

GC-Mass (이론치 : 530.64 g/mol, 측정치 : 530 g/mol) " GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol) "

[합성예 152] Inv-152의 합성 Synthesis Example 152 Synthesis of Inv-152

Figure imgf000232_0001
Figure imgf000232_0001

2-ch 1 or 0-4 , 6-d i pheny 1-1,3,5-tr iazine 대신 2- ( 3-br omopheny 1 ) -4 , 6-d i heny 1-1,3, 5-triazine (3.21 g, 8.26 mmol)을 사용하는 것을 제외하고는 합성예 151과 동일한 과정을 수행하여 Inv-152 (4.14 g, yield ： 78«을 얻었다. 2-ch 1 or 0-4, 6-di pheny 1-1,3,5-tr iazine instead of 2- (3-br omopheny 1) -4, 6-di heny 1-1,3, 5-triazine ( Inv-152 (4.14 g, yield: 78 «was obtained in the same manner as the Synthesis Example 151 except for using 3.21 g and 8.26 mmol).

GC-Mass (이론치: 606.74 g/mol, 측정치: 606 g/mol) GC-Mass (Theoretical value: 606.74 g / mol, Measured value: 606 g / mol)

[합성예 153] Inv-153의 합성 Synthesis Example 153 Synthesis of Inv-153

Figure imgf000232_0002
Figure imgf000232_0002

- phenyl boron ic acid 대신 bi pheny 1-3-ylboronic acid (1.74 g, 8.8 麵이 )을 사용하는 것을 제외하고는 합성예 151과 동일한 과정을 수행하여 상기 중간 화합물  The intermediate compound was prepared in the same manner as in Synthesis Example 151, except for using bi pheny 1-3-ylboronic acid (1.74 g, 8.8 麵) instead of phenyl boron ic acid.

Ιην-153-l (2.58 g, yield ： 86%)을 얻었다. Ιην-153-l (2.58 g, yield: 86%) was obtained.

Inv- 151-1 대신 Inv-153— 1 (2.58 g, 6.88隱 ol)을사용하는 것을 제외하고는 합성예 151과 동일한 과정을 수행하여 목적 화합물인 Inv-153 (3.34 g, yield ： Exv-153— 1 (2.58 g, 6.88 隱 ol) was used instead of Inv-151-1, and the same procedure as in Synthesis Example 151 was carried out to obtain Inv-153 (3.34 g, yield ：

80%)를 얻었다. GC-Mass (이론치 : 606.74 g/mol , 측정치： 606 g/mol) 80%). GC-Mass (Theoretical value: 606.74 g / mol, Measured value: 606 g / mol)

[합성예 154] Inv-154의 합성  Synthesis Example 154 Synthesis of Inv-154

Figure imgf000233_0001
Figure imgf000233_0001

Inv- 151-1 대신 Ιην— 1¾-1 (2.58 g, 6.88 隱 ol)을 사용하는 것올 제외하고는 합성예 152과 동일한 과정을 수행하여 목적 화합물인 Inv-154 (3.24 g, yield ： 69«를 얻었다.  Inv-154 (3.24 g, yield ： 69 «was obtained by the same procedure as in Synthesis Example 152, except that Ιην— 1¾-1 (2.58 g, 6.88 를 ol) was used instead of Inv-151-1. Got it.

GC-Mass (이론치: 682.83 g/mol, 측정치: 682 g/mol)  GC-Mass (Theoretical value: 682.83 g / mol, Measured value: 682 g / mol)

[합성예 155] Inv— 155의 합성  Synthesis Example 155 Synthesis of Inv—155

Figure imgf000233_0002
Figure imgf000233_0002

Inv-155 Inv- 1 55

phenylboro ic acid 대신 3 , 5-d i pheny 1 pheny 1 bor on i c acid (2.41 g, 8.8 mmol)을 사용하는 것올 제외하고는 합성예 151과 동일한 과정을 수행하여 상기 중간화합물 Ιην-155-l (3.29 g, yield ： 91%)을 얻었다.  Except for using 3, 5-di pheny 1 pheny 1 bor on ic acid (2.41 g, 8.8 mmol) instead of phenylboro ic acid, the intermediate compound Ιην-155-l (3.29 g, yield: 91%).

Ιην-151-l 대신 Ιην-155-l (2.58 g, 6.88 麵 ol)을사용하는 것을 제외하고는 합성예 151과 동일한 과정을 수행하여 목적 화합물인 Inv-155 (3.99 g, yield ： 85%)를 얻었다.  Inv-155 (3.99 g, yield: 85%) was obtained by the same procedure as in Synthesis Example 151, except that Ιην-155-l (2.58 g, 6.88 麵 ol) was used instead of Ιην-151-l. Got.

GC-Mass (이론치: 682.83 g/mol, 측정치: 682 g/mol) [합성예 156] Imrl56의 합성 GC-Mass (Theoretical value: 682.83 g / mol, Measured value: 682 g / mol) Synthesis Example 156 Synthesis of Imrl56

Figure imgf000234_0001
Figure imgf000234_0001

Ιην-151-l 대신 Inv— 155-1 (2.58 g, 6.88 mmol)을 사용하는 것을 제외하고는 합성예 152와 동일한 과정올 수행하여 목적 화합물인 Inv— 156 (3.03 g, yield ： 58¾>)를 얻었다.  Inv- 156 (3.03 g, yield: 58¾>) was obtained in the same manner as in Synthesis Example 152, except that Inv- 155-1 (2.58 g, 6.88 mmol) was used instead of Ιην-151-l. Got it.

GC-Mass (이론치: 758.93 g/mol, 측정치: 758 g/mol)  GC-Mass (Theoretical value: 758.93 g / mol, Measured value: 758 g / mol)

[합성예 157] Inv-157의 합성  Synthesis Example 157 Synthesis of Inv-157

Figure imgf000234_0002
Figure imgf000234_0002

IC-353 대신 IC—354 (2.42 g, 8.0 mmol)을 사용하는 것올 제외하고는 합성예 151과동일한 과정올 수행하여 목적 화합물인 Inv-157 (2.72 g, total yield： 64%)을 얻었다.  Except for using IC-354 (2.42 g, 8.0 mmol) instead of IC-353, the same procedure as in Synthesis Example 151 was carried out to obtain Inv-157 (2.72 g, total yield: 64%) as a target compound.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 158] Inv-158의 합성 Synthesis Example 158 Synthesis of Inv-158

Figure imgf000235_0001
Figure imgf000235_0001

Inv-151-1 대신 Inv-157-1 (2.58 g, 6.88 mmol)올 사용하는 것을 제외하고는 합성예 152와 동일한 과정을 수행하여 목적 화합물인 Inv-158 (2.67 g, yield ： 64%)를 얻었다.  Aside from Inv-157-1 (2.58 g, 6.88 mmol) ol instead of Inv-151-1, the same procedure as in Synthesis Example 152 was carried out to obtain Inv-158 (2.67 g, yield: 64%) as a target compound. Got it.

GC-Mass (이론치: 606.74 g/mol, 측정치: 606 g/mol)  GC-Mass (Theoretical value: 606.74 g / mol, Measured value: 606 g / mol)

[합성예 159] Inv~159의 합성  Synthesis Example 159 Synthesis of Inv ~ 159

Figure imgf000235_0002
Figure imgf000235_0002

IC-44 대신 IC-45a (2.42 g, 8.0 mmol)를 사용하는 것을 제외하고는 합성예 153과 동일한 과정을 수행하여 목적 화합물인 Inv-159 (2.80 g, total yield ： 55%)를 얻었다.  Exc-159 (2.80 g, total yield: 55%) was obtained in the same manner as in Synthesis Example 153, except that IC-45a (2.42 g, 8.0 mmol) was used instead of IC-44.

GC-Mass (이론치: 606.74 g/mol, 측정치: 606 g/mol)  GC-Mass (Theoretical value: 606.74 g / mol, Measured value: 606 g / mol)

[합성예 160] Inv-160의 합성  Synthesis Example 160 Synthesis of Inv-160

Figure imgf000235_0003
IC-44 대신 IC-45a (2.42 g, 8.0 讓 ol)를 사용하는 것을 제외하고는 합성예 155와동일한 과정을 수행하여 목적 화합물인 Inv-160 (2.62 g, total yield： 43%)을 얻었다.
Figure imgf000235_0003
Exc-160 (2.62 g, total yield: 43%) was obtained by the same procedure as in Synthesis Example 155, except that IC-45a (2.42 g, 8.0 讓 ol) was used instead of IC-44. .

GC-Mass (이론치 : 758.93 g/mol, 측정치 : 758 g/mol)  GC-Mass (Theoretical value: 758.93 g / mol, Measured value: 758 g / mol)

[합성예 161] Imrl61의 합성  Synthesis Example 161 Synthesis of Imrl61

Figure imgf000236_0001
Figure imgf000236_0001

IC-44 대신 IC—45b (2.42 g, 8.0 mmol)올 사용하는 것을 제외하고는 합성예 151과 동일한 과정을 수행하여 목적 화합물인 Invᅳ 161 (2.42 g, total yield ： 57%)올 얻었다.  Exv 161 (2.42 g, total yield: 57%) of the target compound was obtained by the same procedure as in Synthesis Example 151, except that IC-45b (2.42 g, 8.0 mmol) ol was used instead of IC-44.

GC-Mass (이론치: 530.64 g/mol, 측정치: 530 g/mol)  GC-Mass (Theoretical value: 530.64 g / mol, Measured value: 530 g / mol)

[합성예 162] Inv-162의 합성  Synthesis Example 162 Synthesis of Inv-162

Figure imgf000236_0002
Figure imgf000236_0002

Ιην-151-l 대신 Inv- 161-1 (2.58 g, 6.88 mmol)을사용하는 것을 제외하고는 합성예 152와 동일한 과정을 수행하여 목적 화합물인 Inv-162 (2.55 g, yield ： 61%)를 얻었다.  Inv-162 (2.55 g, yield: 61%) was obtained in the same manner as in Synthesis Example 152 except that Inv-161-1 (2.58 g, 6.88 mmol) was used instead of Ιην-151-l. Got it.

GC-Mass (이론치 : 606.74 g/mol , 측정치: 606 g/mol) [합성예 163] Inv-163의 합성 GC-Mass (Theoretical value: 606.74 g / mol, Measured value: 606 g / mol) Synthesis Example 163 Synthesis of Inv-163

Figure imgf000237_0001
Figure imgf000237_0001

IC-44 대신 IC-45b (2.42 g, 8.0 瞧 ol)를 사용하는 것을 제외하고는 합성예 Synthesis example except for using IC-45b (2.42 g, 8.0 瞧 ol) instead of IC-44

153과동일한 과정을수행하여 목적 화합물인 Inv-163 (2.04 g, total yield： 42%)를 얻었다. The same procedure as 153 was carried out to obtain Inv-163 (2.04 g, total yield: 42%) of the title compound.

GC-Mass (이론치 : 606.74 g/mol, 측정치: 606 g/mol)  GC-Mass (Theoretical value: 606.74 g / mol, Measured value: 606 g / mol)

[합성예 164] Inv-164의 합성  Synthesis Example 164 Synthesis of Inv-164

Figure imgf000237_0002
Figure imgf000237_0002

IC-44 대신 IC_45b (2.42 g, 8.0 画 ol)를 사용하는 것을 제외하고는 합성예 Synthesis example except for using IC_45b (2.42 g, 8.0 μl ol) instead of IC-44

155와동일한 과정을 수행하여 목적 화합물인 Inv-164 (2.85 g, total yield： 47%)을 얻었다. The same procedure as 155 was carried out to obtain Inv-164 (2.85 g, total yield: 47%) as a target compound.

GC-Mass (이론치: 758.93 g/mol, 측정치: 758 g/mol)  GC-Mass (Theoretical value: 758.93 g / mol, Measured value: 758 g / mol)

[합성예 165] Ιην^165의 합성

Figure imgf000238_0001
Synthesis Example 165 Synthesis of Ιην ^ 165
Figure imgf000238_0001

nitrobenzene lnv-165 질소 기류 하에서 화합물인 IC-35 (4.47 g, 20.00 mmol), 2-bromotr iphenylene (9.22 g, 30.00 mmol), Cu powder (0.38 g, 1.00 mmol), K2C03(5.52 g, 40.00 mmol), Na2S04(5.68 g, 40.00 mmol) 및 ni trobenzene(100 ml)를 흔합하고 190°C에서 12시간 동안 교반하였다. 반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgS04를사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 lnv-165 (5.93 g, 수율 66%)을 얻었다. nitrobenzene lnv-165 Compounds IC-35 (4.47 g, 20.00 mmol), 2-bromotr iphenylene (9.22 g, 30.00 mmol), Cu powder (0.38 g, 1.00 mmol), K 2 C0 3 (5.52 g, 40.00 mmol), Na 2 SO 4 (5.68 g, 40.00 mmol) and ni trobenzene (100 ml) were combined and stirred at 190 ° C. for 12 h. After completion of the reaction, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound lnv-165 (5.93 g, 66% yield).

GC-Mass (이론치 : 449.56 g/mol, 측정치: 449 g/mol) [합성예 166] I r-166의 합성 GC-Mass (Theoretical value: 449.56 g / mol, Measured value: 449 g / mol) [Synthesis Example 166] Synthesis of I r-166

Figure imgf000238_0002
Figure imgf000238_0002

nitrobenzene  nitrobenzene

lnv-166  lnv-166

2ᅳ bromotr iphenylene 대신 2- ( 4-br omopheny 1 ) t r i heny 1 ene (11.50 g, 30.0 mmol)을 사용하는 것을 제외하고는 합성예 165와 동일한 과정을 수행하여 lnv-166 (7.04 g, yield ： 67%)올 얻었다. GC-Mass (이론치: 525.66 g/mol, 측정치: 525 g/mol) [합성예 167] Inv-167의 합성 Except for using 2- (4-bromonoy 1) tri heny 1 ene (11.50 g, 30.0 mmol) instead of 2 ᅳ bromotr iphenylene, lnv-166 (7.04 g, yield ： 67%). GC-Mass (Theoretical value: 525.66 g / mol, Measured value: 525 g / mol) Synthesis Example 167 Synthesis of Inv-167

Figure imgf000239_0001
Figure imgf000239_0001

2ᅳ bromotr iphenylene 대신 2- ( 3-br omopheny 1 ) t r i pheny 1 ene (11.50 g, 30.0 mmol)을 사용하는 것을 제외하고는 합성예 165와 동일한 과정을 수행하여 Inv-167 (6.90 g, yield ： 61%)을 얻었다.  Inv-167 (6.90 g, yield ： was performed in the same manner as in Synthesis Example 165 except for using 2- (3-br omopheny 1) tri pheny 1 ene (11.50 g, 30.0 mmol) instead of 2 bromotr iphenylene. 61%).

GC-Mass (이론치: 525.66 g/mol, 측정치: 525 g/mol)  GC-Mass (Theoretical value: 525.66 g / mol, Measured value: 525 g / mol)

[합성예 168] Inv-168의 합성 Synthesis Example 168 Synthesis of Inv-168

Figure imgf000239_0002
Figure imgf000239_0002

nitrobenzene Inv-168  nitrobenzene Inv-168

2一 bromotr iphenylene대신 4- ( 4-br omopheny l)dibenzo[b,d]thi ophene (10.18 g 30.0 mmol)을 사용하는 것을 제외하고는 합성예 165와 동일한 과정을 수행하여 Inv-168 (5.68 g, yield ： 59%)을 얻었다.  Inv-168 (5.68 g) was obtained by the same procedure as in Synthesis Example 165, except that 4- (4-bromopheny l) dibenzo [b, d] thi ophene (10.18 g 30.0 mmol) was used instead of 2 一 bromotr iphenylene. yield: 59%).

GC-Mass (이론치: 481.63 g/mol, 측정치: 481 g/mol)  GC-Mass (Theoretical value: 481.63 g / mol, Measured value: 481 g / mol)

[합성예 169] Inv-169의 합성

Figure imgf000240_0001
Synthesis Example 169 Synthesis of Inv-169
Figure imgf000240_0001

질소 기류 하에서 화합물인 IC-36 (4.47 g, 20.00 mmol), 10-(4-bromophenyl)-9,9-dimethyl-9,10-dihydroacridine (10.93 g, 30.00瞧 ol), Cu powder (0.38 g, 1.00 mmol), K2C03(5.52 g, 40.00 mmol), Na2S04(5.68 g, 40.00 ramol) 및 nitrobenzene(100 ml)를 혼합하고 19CTC에서 12시간 동안 교반하였다. 반웅이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층올 분리한 다음 MgS04를 사용하여 물올 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 lnv-169 (6.38 g, 수율 63%)을 얻었다. IC-36 (4.47 g, 20.00 mmol), 10- (4-bromophenyl) -9,9-dimethyl-9,10-dihydroacridine (10.93 g, 30.00 μl), Cu powder (0.38 g, 1.00 mmol), K 2 CO 3 (5.52 g, 40.00 mmol), Na 2 SO 4 (5.68 g, 40.00 ramol) and nitrobenzene (100 ml) were mixed and stirred at 19 CTC for 12 hours. After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgS0 4 . After removing the solvent of the organic layer was purified by column chromatography to give the target compound lnv-169 (6.38 g, 63% yield).

GC-Mass (이론치 : 506.66 g/mol, 측정치: 506 g/mol)  GC-Mass (Theoretical value: 506.66 g / mol, Measured value: 506 g / mol)

[합성예 170] I L70의 합성  Synthesis Example 170 Synthesis of I L70

Figure imgf000240_0002
Figure imgf000240_0002

10- ( 4-br omopheny 1 ) -9 , 9-d i me t hy 1 -9 , 10-d i hydr oac r i d i ne 대신 Instead of 10- (4-br omopheny 1) -9, 9-d i me t hy 1 -9, 10-d i hydr oac r i d i ne

10- (4-br omopheny 1 ) - ΙΟΗ-pheno t h i az i ne (10.63 g, 30.0 mmol)을 사용하는 것을 제외하고는 합성예 169와동일한 과정을수행하여 lnv-170 (6.85 g, yield ： 69%)을 얻었다. GC-Mass (이론치 : 496.64 g/mol, 측정치 : 496 g/mol) Lnv-170 (6.85 g, yield ： by the same procedure as in Synthesis Example 169, except that 10- (4-br omopheny 1) -ΙΟΗ-pheno thi az i ne (10.63 g, 30.0 mmol) was used. 69%). GC-Mass (Theoretical value: 496.64 g / mol, Measured value: 496 g / mol)

[합성예 171] Inv-1기의 합성  Synthesis Example 171 Synthesis of Inv-1 Group

Figure imgf000241_0001
Figure imgf000241_0001

10- ( 4-bromopheny 1 )-9, 9-d imethyl-9, 10-d i hydroacr idine 대신 10-(4-bromophenyl)-10H-phenoxazine (10.15 g, 30.0 麵 ol)을 사용하는 것을 제외하고는 합성예 169와동일한과정을 수행하여 Inv-171 (6.92 g, yield ： 72%)을 얻었다.  Except for using 10- (4-bromophenyl) -10H-phenoxazine (10.15 g, 30.0 麵 ol) instead of 10- (4-bromopheny 1) -9, 9-d imethyl-9, 10-di hydroacr idine Inv-171 (6.92 g, yield: 72%) was obtained in the same manner as in Synthesis example 169.

GC-Mass (이론치: 480.58 g/mol, 측정치: 480 g/mol)  GC-Mass (Theoretical value: 480.58 g / mol, Measured value: 480 g / mol)

[합성예 172] Inv-172의 합성  Synthesis Example 172 Synthesis of Inv-172

Figure imgf000241_0002
Figure imgf000241_0002

10- ( 4-br omopheny 1 )_9，9ᅳ dimethylᅳ 9， 10ᅳ dihydroacridine 대신 5- ( 4-br omopheny 1 ) - 10-pheny 1 -5 , 10-d i hydr ophenaz i ne (12.40 g, 30.0 mmol)을 사용하는 것을 제외하고는 합성예 169와 동일한 과정을 수행하여 Irw-172 (5.78 g, yield ： 52%)을 얻었다.  10- (4-br omopheny 1) _9，9 ᅳ dimethyl ᅳ 9 ， 10 ᅳ dihydroacridine instead of 5- (4-br omopheny 1)-10-pheny 1 -5, 10-di hydr ophenaz i ne (12.40 g, 30.0 Irw-172 (5.78 g, yield: 52%) was obtained in the same manner as the Synthesis Example 169 except for using mmol).

GC-Mass (이론치: 555.69 g/mol, 측정치: 555 g/mol) [합성예 173] Ιην^173의 합성 GC-Mass (Theoretical value: 555.69 g / mol, Measured value: 555 g / mol) Synthesis Example 173 Synthesis of Ιην ^ 173

Figure imgf000242_0001
Figure imgf000242_0001

IC-35 대신 IC— 37 (4.47 g, 20.0 醒 ol)을 사용하는 것을 제외하고는 합성예 과동일한 과정올 수행하여 lnv-173 (5.30 g, yield ： 59%)을 얻었다.  Except for using IC-37 (4.47 g, 20.0 μl) instead of IC-35, lnv-173 (5.30 g, yield: 59%) was obtained by the same procedure as in Synthesis Example.

GC-Mass (이론치: 449.56 g/mol, 측정치: 449 g/mol)  GC-Mass (Theoretical value: 449.56 g / mol, Measured value: 449 g / mol)

[합성예 174] Inv-174의 합성  Synthesis Example 174 Synthesis of Inv-174

Figure imgf000242_0002
Figure imgf000242_0002

nitrobenzene nv- nitrobenzene nv-

IC-35 대신 IC-37 (4.47 g, 20.0 隱 ol)을 사용하는 것올 제외하고는 합성예 와동일한과정올 수행하여 Inv-174 (6.73 g, yield ： 64%)을 얻었다. Inv-174 (6.73 g, yield: 64%) was obtained in the same manner as the synthesis example except that IC-37 (4.47 g, 20.0 μl) was used instead of IC-35.

GC-Mass (이론치: 525.66 g/mol, 측정치: 525 g/mol)  GC-Mass (Theoretical value: 525.66 g / mol, Measured value: 525 g / mol)

[합성예 175] Inv-175의 합성  Synthesis Example 175 Synthesis of Inv-175

Figure imgf000242_0003
Figure imgf000242_0003

Inv-175  Inv-175

IC-35 대신 IC-39 (4.47 g, 20.0 mmol)를 사용하는 것을 제외하고는 합성예 과동일한과정을 수행하여 Inv-175 (6.41 g, yield ： 61%)을 얻었다. Synthesis example except for using IC-39 (4.47 g, 20.0 mmol) instead of IC-35 The same procedure was followed to obtain Inv-175 (6.41 g, yield: 61%).

GC-Mass (이론치 : 525.66 g/mol, 측정치 : 525 g/mol)  GC-Mass (Theoretical value: 525.66 g / mol, Measured value: 525 g / mol)

[합성예 176] In\ L76의 합성  Synthesis Example 176 Synthesis of In \ L76

Figure imgf000243_0001
Figure imgf000243_0001

IC-35 대신 IC-39 (4.47 g, 2().0 mmol)를 사용하는 것을 제외하고는 합성예 와동일한 과정을수행하여 Inv-176 (6.36 g, yield ： 66%)을 얻었다.  Inv-176 (6.36 g, yield: 66%) was obtained in the same manner as the synthesis example except that IC-39 (4.47 g, 2 (). 0 mmol) was used instead of IC-35.

GC-Mass (이론치: 481.63 g/mol, 측정치: 481 g/mol)  GC-Mass (Theoretical value: 481.63 g / mol, Measured value: 481 g / mol)

[합성예 177] Inv-177의 합성  Synthesis Example 177 Synthesis of Inv-177

Figure imgf000243_0002
Figure imgf000243_0002

IC-36 대신 IC-38 (4.47 g, 20.0 隱 ol)를 사용하는 것을 제외하고는 합성예 와동일한 과정을수행하여 Inv-177 (6.69 g, yield ： 66%)을 얻었다.  Inv-177 (6.69 g, yield: 66%) was obtained in the same manner as the synthesis example except that IC-38 (4.47 g, 20.0 μl ol) was used instead of IC-36.

GC-Mass (이론치: 506.66 g/mol, 측정치: 506 g/mol)  GC-Mass (Theoretical value: 506.66 g / mol, Measured value: 506 g / mol)

[합성예 178] Inv-178의 합성 Synthesis Example 178 Synthesis of Inv-178

Figure imgf000244_0001
Figure imgf000244_0001

IC-36 대신 IC-38 (4.47 g, 20.0 mmol)를 사용하는 것을 제외하고는 합성예 170과 동일한 과정을 수행하여 Inv-178 (5.36 g, yield ： 54%)을 얻었다 .GC-Mass (이론치 : 496.64 g/mol , 측정치: 496 g/mol)  Exv-178 (5.36 g, yield: 54%) was obtained by the same procedure as Synthesis Example 170 except for using IC-38 (4.47 g, 20.0 mmol) instead of IC-36. GC-Mass (Theoretical Value) : 496.64 g / mol, found: 496 g / mol)

[합성예 179] Inv-179의 합성  Synthesis Example 179 Synthesis of Inv-179

Figure imgf000244_0002
Figure imgf000244_0002

IC-36 대신 IC-40 (4.47 g, 20.0 画 ol)를 사용하는 것올 제외하고

Figure imgf000244_0003
1기과동일한 과정을 수행하여 Inv-179 (5.86 g, yield ： 61«을 얻었다. Except for using IC-40 (4.47 g, 20.0 μl ol) instead of IC-36
Figure imgf000244_0003
Inv-179 (5.86 g, yield: 61 «was obtained by the same procedure as in the first stage.

GC-Mass (이론치 : 480.58 g/mol , 축정치: 480 g/mol)  GC-Mass (Theoretical value: 480.58 g / mol, Accumulated value: 480 g / mol)

[합성예 180] Im l80의 합성  Synthesis Example 180 Synthesis of Im l80

Figure imgf000244_0004
Figure imgf000244_0004

IC-36 대신 IC-40 (4.47 g, 20.0 画 ol)를 사용하는 것을 제외하고는 합성예 과동일한 과정을 수행하여 Inv-180 (7.11 g, yield ： 64«을 얻었다. Synthesis example except for using IC-40 (4.47 g, 20.0 μl ol) instead of IC-36 The same procedure was followed to obtain Inv-180 (7.11 g, yield ： 64 «.

GC-Mass (이론치 : 555.69 g/mol, 측정치 : 555 g/mol)  GC-Mass (Theoretical value: 555.69 g / mol, Measured value: 555 g / mol)

[합성예 181] Inv-181의 합성  Synthesis Example 181 Synthesis of Inv-181

Figure imgf000245_0001
Figure imgf000245_0001

IC-35 대신 ICᅳ 41 (4.47' g, 20.0 mmol)을 사용하는 것을 제외하고는 합성예 와동일한 과정을수행하여 Inv-181 (5.30 g, yield ： 59%)을 얻었다. Inv-181 (5.30 g, yield: 59%) was obtained in the same manner as the synthesis example except for using IC ᅳ 41 (4.47 ′ g, 20.0 mmol) instead of IC-35.

GC-Mass (이론치: 449.56 g/mol, 측정치: 449 g/mol)  GC-Mass (Theoretical value: 449.56 g / mol, Measured value: 449 g / mol)

[합성예 182] I l82의 합성  Synthesis Example 182 Synthesis of I l82

Figure imgf000245_0002
Figure imgf000245_0002

IC-35 대신 IC-41 (4.47 g, 20.0 mmol)을 사용하는 것을 제외하고는 합성예 과동일한과정을 수행하여 Inv-182 (6.62 g, yield ： 65%)을 얻었다.  Inv-182 (6.62 g, yield: 65%) was obtained by the same procedure as in Synthesis Example, except that IC-41 (4.47 g, 20.0 mmol) was used instead of IC-35.

GC-Mass (이론치 : 525.66 g/mol , 측정치 : 525 g/mol)  GC-Mass (Theoretical value: 525.66 g / mol, Measured value: 525 g / mol)

[합성예 183] Inv-183의 합성 Synthesis Example 183 Synthesis of Inv-183

Figure imgf000246_0001
Figure imgf000246_0001

IC-35 대신 IC-42b (4.47 g, 20.0睡 ol)를사용하는 것을 제외하고는 합성예 과동일한과정을수행하여 Inv-183 (6.31 g, yield ： 64%)을 얻었다. Inv-183 (6.31 g, yield: 64%) was obtained in the same manner as in Synthesis Example, except that IC-42b (4.47 g, 20.0 μl) was used instead of IC-35.

GC-Mass (이론치 : 525.66 g/raol , 측정치 : 525 g/mol)  GC-Mass (Theoretical value: 525.66 g / raol, Measured value: 525 g / mol)

[합성예 184] Inv-184의 합성  Synthesis Example 184 Synthesis of Inv-184

Figure imgf000246_0002
Figure imgf000246_0002

IC-35 대신 IC-42b (4.47 g, 20.0誦 ol)를 사용하는 것을 제외하고는 합성예 과 동일한과정을 수행하여 Inv-184 (5.59 g, yield ： 58%)을 얻었다.  Inv-184 (5.59 g, yield: 58%) was obtained in the same manner as the synthesis example except that IC-42b (4.47 g, 20.0 μl ol) was used instead of IC-35.

GC-Mass (이론치: 481.63 g/mol, 측정치: 481 g/mol)  GC-Mass (Theoretical value: 481.63 g / mol, Measured value: 481 g / mol)

[합성예 185] Inv-185의 합성  Synthesis Example 185 Synthesis of Inv-185

Figure imgf000246_0003
Figure imgf000246_0003

IC-36 대신 IC-42a (4.47 g, 20.0議 ol)를사용하는 것을 제외하고는 합성예 와동일한과정을 수행하여 Inv-185 (5.68 g, yield ： 56%)올 얻었다. GC- ass (이론치 : 506.66 g/mol , 측정치: 506 g/mol) Inv-185 (5.68 g, yield: 56%) was obtained in the same manner as in Synthesis Example, except that IC-42a (4.47 g, 20.0 μl) was used instead of IC-36. GC-ass (Theoretical value: 506.66 g / mol, Measured value: 506 g / mol)

[합성예 186] Inv-186의 합성  Synthesis Example 186 Synthesis of Inv-186

Figure imgf000247_0001
Figure imgf000247_0001

IC-36 대신 IC-42a (4.47 g, 20.0 mmol)를사용하는 것을 제외하고는 합성예 170과 동일한 과정을 수행하여 Inv-186 (5.86 g, yield ： 59%)을 얻었다.  Inv-186 (5.86 g, yield: 59%) was obtained in the same manner as the Synthesis Example 170 except for using IC-42a (4.47 g, 20.0 mmol) instead of IC-36.

GC-Mass (이론치 : 496.64 g/mol , 측정치: 496 g/mol)  GC-Mass (Theoretical value: 496.64 g / mol, Measured value: 496 g / mol)

[합성예 187] I l87의 합성  Synthesis Example 187 Synthesis of I l87

Figure imgf000247_0002
Figure imgf000247_0002

IC-36 대신 IC-32a (4.47 g, 20.0麵 ol)를 사용하는 것을 제외하고는 합성예 Γ기과 동일한과정을 수행하여 Inv-187 (5.86 g, yield ： 61%)올 얻었다.  Inv-187 (5.86 g, yield: 61%) was obtained in the same manner as the synthesis example Γ except for using IC-32a (4.47 g, 20.0 μl ol) instead of IC-36.

GC-Mass (이론치: 480.58 g/mol, 측정치: 480 g/mol)  GC-Mass (Theoretical value: 480.58 g / mol, Measured value: 480 g / mol)

[합성예 188] Inv-188의 합성 Synthesis Example 188 Synthesis of Inv-188

Figure imgf000248_0001
Figure imgf000248_0001

IC-36 대신 IC-32a (4.47 g, 20.0薩 ol)를 사용하는 것을 제외하고는 합성예 와동일한 과정을 수행하여 Inv-188 (6.33 g, yield ： 57%)을 얻었다.  Inv-188 (6.33 g, yield: 57%) was obtained by the same procedure as in Synthesis Example, except that IC-32a (4.47 g, 20.0 μl) was used instead of IC-36.

GC-Mass (이론치： 555.69 g/mol, 측정치: 555 g/mol)  GC-Mass (Theoretical value: 555.69 g / mol, Measured value: 555 g / mol)

[합성예 189] Inv-189의 합성  Synthesis Example 189 Synthesis of Inv-189

Figure imgf000248_0002
Figure imgf000248_0002

IC-35 대신 IC_32b (4.47 g, 20.0睡 ol)을 사용하는 것을 제외하고는 합성예 동일한 과정을 수행하여 Inv— 189 (6.89 g, yield ： 69W을 얻었다.  Exv. 189 (6.89 g, yield: 69W) was obtained in the same manner as in Synthesis Example, except that IC_32b (4.47 g, 20.0 μl) was used instead of IC-35.

GC-Mass (이론치: 449.56 g/mol, 측정치: 449 g/mol)  GC-Mass (Theoretical value: 449.56 g / mol, Measured value: 449 g / mol)

[합성예 190] I 190의 합성  Synthesis Example 190 Synthesis of I 190

Figure imgf000248_0003
Figure imgf000248_0003

IC-35 대신 IC-32b (4.47 g, 20.0圆 ol)을 사용하는 것을 제외하고는 합성예 과동일한 과정을 수행하여 Inv-190 (5.68 g, yield ： 54%)을 얻었다. GC-Mass (이론치 : 525.66 g/mol, 측정치: 525 g/mol) Inv-190 (5.68 g, yield: 54%) was obtained by the same procedure as in Synthesis Example, except that IC-32b (4.47 g, 20.0 μl ol) was used instead of IC-35. GC-Mass (Theoretical value: 525.66 g / mol, Measured value: 525 g / mol)

[합성예 191] Inv~191의 합성  Synthesis Example 191 Synthesis of Inv ~ 191

Figure imgf000249_0001
Figure imgf000249_0001

IC-35 대신 Ιην-151-l (5.98 g, 20.0 mmol)을 사용하는 것을 제외하고는 합성예 167과동일한과정올 수행하여 Inv-191 (7.34 g, yield ： 61%)을 얻었다.  Inv-191 (7.34 g, yield: 61%) was obtained by the same procedure as in Synthesis Example 167 except that ηη-151-l (5.98 g, 20.0 mmol) was used instead of IC-35.

GC-Mass · (이론치 : 601.76 g/mol , 측정치 : 601 g/mol)  GC-Mass · (Theoretical value: 601.76 g / mol, Measured value: 601 g / mol)

[합성예 192] Inv L92의 합성  Synthesis Example 192 Synthesis of Inv L92

Figure imgf000249_0002
Figure imgf000249_0002

IC-35 대신 Ιην-151-l (5.98 g, 20.0 匪 ol)을 사용하는 것을 제외하고는 합성예 168과 동일 ： 과정을 수행하여 Inv-192 (7.70 g, yield ： 69%)을 얻었다.  Inv-192 (7.70 g, yield: 69%) was obtained in the same manner as in Synthesis Example 168 except that ηη-151-l (5.98 g, 20.0 μl ol) was used instead of IC-35.

GC-Mass (이론치: 557.73 g/mol, 측정치: 557 g/mol)  GC-Mass (Theoretical value: 557.73 g / mol, Measured value: 557 g / mol)

[합성예 193] Inv-193의 합성  Synthesis Example 193 Synthesis of Inv-193

Figure imgf000249_0003
IC-36 대신 IC-43 (4.47 g, 20.0 麵 ol)를 사용하는 것을 제외하고는 합성예 169와동일한과정을수행하여 Inv-193 (6.69 g, yield ： 66«을 얻었다.
Figure imgf000249_0003
Inv-193 (6.69 g, yield: 66 «was obtained by the same procedure as in Synthesis Example 169 except that IC-43 (4.47 g, 20.0 μl) was used instead of IC-36.

GC-Mass (이론치 : 506.66 g/mol, 측정치: 506 g/mol)  GC-Mass (Theoretical value: 506.66 g / mol, Measured value: 506 g / mol)

[합성예 194] Inv~194의 합성  Synthesis Example 194 Synthesis of Inv ~ 194

Figure imgf000250_0001
Figure imgf000250_0001

IC-36 대신 IC-43 (4,47 g, 20.0 誦 ol)를 사용하는 것을 제외하고는 합성예 170과동일한 과정을 수행하여 Inv-194 (5.66 g, yield ： 57%)을 얻었다.  Inv-194 (5.66 g, yield: 57%) was obtained in the same manner as Synthesis Example 170 except for using IC-43 (4,47 g, 20.0 μl ol) instead of IC-36.

GC-Mass (이론치 : 496.64 g/mol , 측정치 : 496 g/mol)  GC-Mass (Theoretical value: 496.64 g / mol, Measured value: 496 g / mol)

[합성예 195] Ιην^195의 합성  Synthesis Example 195 Synthesis of Ιην ^ 195

Figure imgf000250_0002
Figure imgf000250_0002

IC-36.대신 Ιην-153-l (5.98 g, 20.0 mmol)을 사용하는 것을 제외하고는 합성예 1기과 동일한 과정을 수행하여 Inv- 195 (8.10 g, yield ： 64%)을 얻었다.  Inv-195 (8.10 g, yield: 64%) was obtained in the same manner as in Synthesis Example 1 except that ηη-153-l (5.98 g, 20.0 mmol) was used instead of IC-36.

GC-Mass (이론치: 632.77 g/mol, 측정치: 632 g/mol)  GC-Mass (Theoretical value: 632.77 g / mol, Measured value: 632 g / mol)

[합성예 196] 1지96의 합성 Synthesis Example 196 Synthesis of 196

Figure imgf000251_0001
Figure imgf000251_0001

IC-36 대신 Inv— 153-1 (5.98 g, 20.0 ramol)을 사용하는 것을 제외하고 합성예 172와동일한 과정을 수행하여 Inv- 196 (7.65 g, yield ： 54%)을 얻었다.  Inv-196 (7.65 g, yield: 54%) was obtained in the same manner as in Synthesis Example 172 except that Inv-153-1 (5.98 g, 20.0 ramol) was used instead of IC-36.

GC-Mass (이론치 : 707.88 g/mol, 측정치 : 707 g/mol)  GC-Mass (Theoretical value: 707.88 g / mol, Measured value: 707 g / mol)

[합성예 197] Imr497의 합성  Synthesis Example 197 Synthesis of Imr497

Figure imgf000251_0002
Figure imgf000251_0002

IC-35 대신 Ιην-155-l (9.03 g, 20.0 mmol)올 사용하는 것을 제외하고는 합성예 165와동일한과정을 수행하여 Inv-197 (8.41 g, yield ： 62%)을 얻었다.  Inv-197 (8.41 g, yield: 62%) was obtained in the same manner as Synthesis Example 165 except for using ηη-155-l (9.03 g, 20.0 mmol) ol instead of IC-35.

GC-Mass (이론치 : 677.85 g/mol , 측정치 : 677 g/mol)  GC-Mass (Theoretical value: 677.85 g / mol, Measured value: 677 g / mol)

[합성예 198] Inv-198의 합성  Synthesis Example 198 Synthesis of Inv-198

Figure imgf000251_0003
Figure imgf000251_0003

•IC-35 대신 Ιην-155-l (9.03 g, 20.0 薩 ol)을 사용하는 것을 제외하고는 합성예 166과 동일한 과정을 수행하여 Inv-198 (9.95 g, yield ： 66%)을 얻었다. GC-Mass (이론치: 753.95 g/mol, 측정치: 753 g/mol) • Except for using Ιην-155-l (9.03 g, 20.0 μl) instead of IC-35 Inv-198 (9.95 g, yield: 66%) was obtained in the same manner as in Synthesis example 166. GC-Mass (Theoretical value: 753.95 g / mol, Measured value: 753 g / mol)

[합성예 199] Inv-199의 합성  Synthesis Example 199 Synthesis of Inv-199

Figure imgf000252_0001
Figure imgf000252_0001

IC-35 대신 Ιην-159-l (7.51 g, 20.0 瞧 ol)을 사용하는 것을 제외하고는 합성예 167과 동일한과정을수행하여 Inv-199 (8.54 g, yield ： 63%)을 얻었다.  Inv-199 (8.54 g, yield: 63%) was obtained in the same manner as in Synthesis Example 167 except that ηη-159-l (7.51 g, 20.0 μl ol) was used instead of IC-35.

GC-Mass (이론치 : 677.85 g/mol , 측정치 : 677 g/mol)  GC-Mass (Theoretical value: 677.85 g / mol, Measured value: 677 g / mol)

[합성예 200] Inv-200의 합성  Synthesis Example 200 Synthesis of Inv-200

Figure imgf000252_0002
Figure imgf000252_0002

IC-35 대신 Ιην-159-l (9.03 g, 20.0 睡 ol)을 사용하는 것을 제외하고는 합성예 168과 ^일한과정을 수행하여 Inv-200 (8.52 g, yield ： 6OT)을 얻었다.  Inv-200 (8.52 g, yield: 6OT) was obtained by performing the same procedure as in Synthesis Example 168 except that ηη-159-l (9.03 g, 20.0 μl ol) was used instead of IC-35.

GC-Mass (이론치: 709.92 g/mol, 측정치: 709 g/mol)  GC-Mass (Theoretical value: 709.92 g / mol, Measured value: 709 g / mol)

[합성예 201] Inv-2()1의 합성 Synthesis Example 201 Synthesis of Inv-2 () 1

Figure imgf000253_0001
Figure imgf000253_0001

IC-36 대신 Inv-157-1 (5.98 g, 20.0 讓 ol)을 사용하는 것을 제외하고는 합성예 169와동일한과정을 수행하여 I.nv-201 (6.18 g, yield ： 53%)을 얻었다.  I.nv-201 (6.18 g, yield: 53%) was obtained in the same manner as Synthesis Example 169 except for using Inv-157-1 (5.98 g, 20.0 μl ol) instead of IC-36.

GC-Mass (이론치 : 582.76 g/mol, 측정치 : 582 g/mol)  GC-Mass (Theoretical value: 582.76 g / mol, Measured value: 582 g / mol)

[합성예 202] Im 202의 합성  Synthesis Example 202 Synthesis of Im 202

Figure imgf000253_0002
Figure imgf000253_0002

IC-36 대신 Inv-15그 1 (5.98 g, 20.0 隱 ol)올 사용하는 것올 제외하고는 합성예 170과동일한 과정을수행하여 Inv-202 (5.84 g, yield ： 51%)을 얻었다.  Inv-202 (5.84 g, yield: 51%) was obtained in the same manner as in Synthesis Example 170, except that Inv-15I 1 (5.98 g, 20.0 μl) was used instead of IC-36.

GC-Mass (이론치: 572.74 g/mol, 측정치: 572 g/mol)  GC-Mass (Theoretical value: 572.74 g / mol, Measured value: 572 g / mol)

[합성예 203] Im 203의 합성  Synthesis Example 203 Synthesis of Im 203

Figure imgf000253_0003
Figure imgf000253_0003

1C-36 대신 Inv- 161-1 (5.98 g, 20.0 画 ol)을 사용하는 것을 제외하고는 합성예 1기과 동일한 과정을 수행하여 Inv-203 (7.46 g, yield ： 67%)을 얻었다. GC-Mass (이론치 : 556.67 g/mol , 측정치 : 556 g/mol) Except for using Inv-161-1 (5.98 g, 20.0 μl ol) instead of 1C-36 Inv-203 (7.46 g, yield: 67%) was obtained in the same manner as in Synthesis example 1. GC-Mass (Theoretical value: 556.67 g / mol, Measured value: 556 g / mol)

[합성예 204] I 204의 합성  Synthesis Example 204 Synthesis of I 204

Figure imgf000254_0001
Figure imgf000254_0001

nitrobenzene  nitrobenzene

IC-36 대신 Inv-163-l (7.51 g, 20.0 mmol)을 사용하는 것을 제외하고는 합성예 172와동일한 과정을 수행하여 lnv-204 (9.06 g, yield ： 64%)을 얻었다.  Except for using Inv-163-l (7.51 g, 20.0 mmol) instead of IC-36 was carried out the same procedure as in Synthesis Example 172 to obtain lnv-204 (9.06 g, yield: 64%).

GC-Mass (이론치: 707.88 g/mol, 측정치: 707 g/mol)  GC-Mass (Theoretical value: 707.88 g / mol, Measured value: 707 g / mol)

[합성예 205] Inv- 205의 합성  Synthesis Example 205 Synthesis of Inv-205

Figure imgf000254_0002
Figure imgf000254_0002

질소 기류 하에서 IC-46 (3 14.48 mmol) IC-46 (3 14.48 mmol) under nitrogen stream

2- ( 3-ch 1 or opheny 1 ) -4 , 6-d i heny 1 - 1 , 3 , 5- 1 r i az i ne (5.97 g, 17.37 mmol), Pd(0Ac)2 (0.16 g, 5 mol ), NaO(t-bu) (2.78 g, 28.95 mmol), P(t-bu)3 (0.29 g, 1.45 mmol) 및 Toluene (100 ml)을 흔합하고 110°C에서 12시간동안교반하였다. 2- (3-ch 1 or opheny 1) -4, 6-di heny 1-1, 3, 5- 1 ri az i ne (5.97 g, 17.37 mmol), Pd (0Ac) 2 (0.16 g, 5 mol ), NaO (t-bu) (2.78 g, 28.95 mmol), P (t-bu) 3 (0.29 g, 1.45 mmol) and Toluene (100 ml) were combined and stirred at 110 ° C for 12 h.

반웅이 종결된 후 에틸아세테이트로 추출한 다음 MgS04로 수분을 제거하고， 컬럼크로마토그래피 (Hexane:EA = 2:1 (v/v))로 정제하여 Inv-205 (5.59 g, 수율After the reaction was completed, the resultant was extracted with ethyl acetate, followed by removal of water with MgS0 4 , and purification with column chromatography (Hexane: EA = 2: 1 (v / v)) to obtain Inv-205 (5.59 g, yield).

75 을 얻었다. GC-Mass (이론치 : 514.18 g/mol , 측정치 : 514 g/mol) 75 was obtained. GC-Mass (Theoretical value: 514.18 g / mol, Measured value: 514 g / mol)

[합성예 206] Inv-206의 합성  Synthesis Example 206 Synthesis of Inv-206

Figure imgf000255_0001
Figure imgf000255_0001

IC-46대신 IC-47를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을 수행하여 목적 화합물인 Inv-206 (5.29 g, 71 %)를 얻었다.  Exc-206 (5.29 g, 71%) was obtained by the same procedure as in Synthesis Example 205, except that IC-47 was used instead of IC-46.

GC-Mass (이론치: 514.18 g/mol, 측정치: 514 g/mol)  GC-Mass (Theoretical value: 514.18 g / mol, Measured value: 514 g / mol)

[합성예 207] Inv-207의 합성  Synthesis Example 207 Synthesis of Inv-207

Figure imgf000255_0002
Figure imgf000255_0002

IC-46대신 IC-48를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을수행하여 목적 화합물인 Inv-207 (5.44 g, 73 %)를 얻었다.  Exc-207 (5.44 g, 73%) was obtained by the same procedure as in Synthesis Example 205, except that IC-48 was used instead of IC-46.

GC-Mass (이론치: 514.18 g/mol, 측정치: 514 g/mol)  GC-Mass (Theoretical value: 514.18 g / mol, Measured value: 514 g / mol)

[합성예 208] Inv-208의 합성 Synthesis Example 208 Synthesis of Inv-208

Figure imgf000256_0001
Figure imgf000256_0001

IC-46대신 IC— 49를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을 수행하여 목적 화합물인 Inv— 208 (4.62 g, 69 %)를 얻었다.  Ex. 208 (4.62 g, 69%) was obtained by the same procedure as in Synthesis Example 205, except that IC-49 was used instead of IC-46.

GC-Mass (이론치 : 556.21 g/mol, 측정치: 556 g/mol)  GC-Mass (Theoretical value: 556.21 g / mol, Measured value: 556 g / mol)

[합성예 209] Inv-209의 합성  Synthesis Example 209 Synthesis of Inv-209

Figure imgf000256_0002
Figure imgf000256_0002

IC-46대신 IC-50를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을수행하여 목적 화합물인 Inv-209 (3.66 g, 67 %)를 얻었다.  Exc-209 (3.66 g, 67%) was obtained by the same procedure as in Synthesis Example 205, except that IC-50 was used instead of IC-46.

GC-Mass (이론치: 680.24 g/mol, 측정치: 680 g/mol)  GC-Mass (Theoretical value: 680.24 g / mol, Measured value: 680 g / mol)

[합성예 210] Inv-210의 합성 Synthesis Example 210 Synthesis of Inv-210

Figure imgf000257_0001
Figure imgf000257_0001

IC-46대신 IC-51를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을 수행하여 목적 화합물인 Inv— 210 (4.87 g, 76 %)를 얻었다.  Exc. 210 (4.87 g, 76%) was obtained by the same procedure as in Synthesis Example 205, except that IC-51 was used instead of IC-46.

GC-Mass (이론치 : 578.10 g/mol, 측정치: 578 g/mol)  GC-Mass (Theoretical value: 578.10 g / mol, Measured value: 578 g / mol)

[합성예 211] Inv~211의 합성  Synthesis Example 211 Synthesis of Inv ~ 211

Figure imgf000257_0002
Figure imgf000257_0002

IC-46 대신 IC-52를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을수행하여 목적 화합물인 Inv-211 (4.75 g, 74 %)를 얻었다.  Exc-211 (4.75 g, 74%) was obtained by the same procedure as in Synthesis Example 205, except that IC-52 was used instead of IC-46.

GC-Mass (이론치: 578.10 g/mol, 측정치: 578 g/mol)  GC-Mass (Theoretical value: 578.10 g / mol, Measured value: 578 g / mol)

[합성예 212] Inv-212의 합성 Synthesis Example 212 Synthesis of Inv-212

Figure imgf000258_0001
Figure imgf000258_0001

IC-46 대신 IC-53를 사용하는 것을 제외하고는 상기 합성예 205과 동일한 과정을수행하여 목적 화합물인 Inv-212 (4.68 g, 73 %)를 얻었다.  Exc-212 (4.68 g, 73%) was obtained by the same procedure as in Synthesis Example 205, except that IC-53 was used instead of IC-46.

GC-Mass (이론치 : 578.10 g/mol, 측정치 : 578 g/mol)  GC-Mass (Theoretical value: 578.10 g / mol, Measured value: 578 g / mol)

[합성예 213] In\ 213의 합성  Synthesis Example 213 Synthesis of In \ 213

Figure imgf000258_0002
Figure imgf000258_0002

2-(3'-chlorobi pheny 1ᅳ 3ᅳ y 1 )-4, 6一 d i pheny 1一 1 , 3， 5ᅳ t r i az i ne을 사용하는 것을 제외하고 합성예 29와동일한 과정을 수행하여 목적 화합물인 hw-213 (4.31 g,수율 61 %)을 얻었다. The same procedure as in Synthesis Example 29 was carried out except that 2- (3'-chlorobi pheny 1 ᅳ 3 ᅳ y 1) -4, 6 一 di pheny 1 一 1, 3, 5 ᅳ tri az i ne was used. Obtained the target compound hw-213 (4.31 g, 61% yield).

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol)

[합성예 214] Inv-214의 합성 Synthesis Example 214 Synthesis of Inv-214

Figure imgf000259_0001
Figure imgf000259_0001

2ᅳ ( 3ᅳ ch 1 oropheny 1 )-4, 6-d i pheny 1-1,3,5-triazine 대신 2-(3'-chlorobi pheny 1 -4-y 1 )— 4 , 6-d i pheny 1 - 1 , 3， 5- 1 r i az i ne을 사용하는 것을 제외하고 합성예 29와동일한 과정을 수행하여 목적 화합물인 Inv-214 (4.10 g,수율 58 %)을 얻었다.  2 ((3 ᅳ ch 1 oropheny 1) -4, 6-di pheny 1-1,3,5-triazine instead of 2- (3'-chlorobi pheny 1 -4-y 1) — 4, 6-di pheny 1 Inv-214 (4.10 g, Yield 58%) was obtained by the same procedure as in Synthesis Example 29, except that 1, 3, 5- 1 ri az i ne was used.

GOMass (이론치: 665.26 g/raol, 축정치: 665 g/mol)  GOMass (Theoretical value: 665.26 g / raol, Accumulated value: 665 g / mol)

[합성예 215] Inv-215의 합성  Synthesis Example 215 Synthesis of Inv-215

Figure imgf000259_0002
Figure imgf000259_0002

2- ( 3-ch 1 oropheny 1 )ᅳ 4 , 6-d i pheny 1-1,3,5-triazine 대신 2-(4' -ch lorobi pheny 1— 3— y 1 )一 4， 6-d i pheny l—l'3'5—triazine을 사용하는 것을 제외하고 합성예 29와동일한 과정올 수행하여 목적 화합물인 Inv-215 (4.66 g,수율 66 D을 얻었다. 2- (3-ch 1 oropheny 1) ᅳ 4, 6-di pheny Instead of 1-1,3,5-triazine 2- (4 '-ch lorobi pheny 1— 3— y 1) 一 4 ， 6-di pheny Except for using l—l ′ 3′5—triazine, the same procedure as in Synthesis Example 29 was carried out to obtain Inv-215 (4.66 g, 66 D) as a target compound.

GC-Mass (이론치: 665.26 g/mol, 측정치: 665 g/mol) [합성예 216] Inv^216의 합성 GC-Mass (Theoretical value: 665.26 g / mol, Measured value: 665 g / mol) Synthesis Example 216 Synthesis of Inv ^ 216

Figure imgf000260_0001
Figure imgf000260_0001

2- (3-chl or opheny 1 )-4, 6ᅳ d i pheny 1-1,3,5-triazine 대신 2-(4'-chlorobipheny卜 4-yl)-4,6-dipheny卜 l,3,5-triazine올 사용하는 것을 제외하고 합성예 29와동일한과정을 수행하여 목적 화합물인 Inv-216 (4.24 g,수율 60 «을 얻었다.  2- (3-chl or opheny 1) -4, 6 ᅳ di pheny 1-1,3,5-triazine instead of 2- (4'-chlorobipheny 卜 4-yl) -4,6-dipheny 卜 l, 3, Except for using 5-triazineol was carried out the same procedure as in Synthesis Example 29 to obtain the target compound Inv-216 (4.24 g, yield 60 «.

GC-Mass (이론치: 665.26 g/mol, 축정치: 665 g/mol)  GC-Mass (Theoretical value: 665.26 g / mol, Accumulated value: 665 g / mol)

[합성예 217] Inv-217의 합성  Synthesis Example 217 Synthesis of Inv-217

Figure imgf000260_0002
Figure imgf000260_0002

2-(3-chlorophenyl )-4, 6-di pheny 1-1,3,5-triazine 대신 2-(7-chloro-9,9-dimethyl-9H-fluoren-2-yl)-4,6-diphenyl-l,3,5-triazine 을 사용하는 것을 제외하고 합성예 29와 동일한 과정을 수행하여 목적 화합물인 Inv-217 (4.12 g, 수율 55 %)을 얻었다.  2- (3-chlorophenyl) -4, 6-di pheny 1-1,3,5-triazine instead of 2- (7-chloro-9,9-dimethyl-9H-fluoren-2-yl) -4,6- Except for using diphenyl-l, 3,5-triazine was carried out in the same manner as in Synthesis Example 29 to obtain the target compound Inv-217 (4.12 g, 55% yield).

GC-Mass (이론치: 705.29 g/mol, 측정치: 705 g/mol) [합성예 218] Inv-218의 합성 GC-Mass (Theoretical value: 705.29 g / mol, Measured value: 705 g / mol) Synthesis Example 218 Synthesis of Inv-218

Figure imgf000261_0001
Figure imgf000261_0001

IC-la 대신 준비예 1에서 제조한 또 다른 화합물인 IC-lb를 사용하고， 2-br omo-4 , 6~d i pheny 1 py r i d i ne 대신 2一( 6_br omod i benzo [ b,d]thi ophen-4-y 1 )-4, 6—d i pheny 1—1， 3， 5_t r i az i ne를 사용하는 것을 제외하고는 합성예 1과 동일한과정을수행하여 목적 화합물인 Inv-218(4.67 g 수율 38«을 얻었다. Instead of IC-la, another compound prepared in Preparation Example 1, IC-lb, was used, and instead of 2-br omo-4, 6 ~ di pheny 1 py ridi ne, 2 一 (6_br omod i benzo [b, d] thi Ophen-4-y 1) -4, 6—di pheny 1—1, 3, 5_t ri az i ne was followed by the same procedure as in Synthesis Example 1 to obtain Inv-218 (4.67 g) as a target compound. Yield 38 «.

GC-Mass (이론치: 695.21g/mol, 측정치: 695 g/mol)  GC-Mass (Theoretical value: 695.21 g / mol, Measured value: 695 g / mol)

[합성예 219] Inv"219의 합성  Synthesis Example 219 Synthesis of Inv "219

Figure imgf000261_0002
Figure imgf000261_0002

IC-la 대신 준비예 1에서 제조한 또다른 화합물인 IC-lb를 사용하고， Instead of IC-la, another compound prepared in Preparation Example 1 is used, IC-lb,

2- br omo-4 , 6~d i pheny 1 py r i d i ne 대신2- br omo-4, 6 ~ di pheny 1 py ridi ne instead

3- bromo-6-(4 , 6~di pheny 1-1 ,3,5-triazi η-2-yl ) -9-pheny 1 -9H~car bazo 1 e를 사용하는 것을 제외하고는 합성예 1과동일한 과정을 수행하여 목적 화합물인 Inv-219(5.34 g 수율 40%)올 얻었다. GC-Mass (이론치: 754.28g/mol, 측정치: 754 g/mol) [실시예 1 ~ 30] 유기 전계 발광소자의 제작 Synthesis Example 1 except that 3-bromo-6- (4, 6 to di pheny 1-1,3,5-triazi η-2-yl) -9-pheny 1 -9H to car bazo 1 e were used. The same procedure was followed to obtain Inv-219 (5.34 g yield 40%) as the target compound. GC-Mass (Theoretical value: 754.28g / mol, Measured value: 754 g / mol) [Examples 1 to 30] Fabrication of Organic Electroluminescent Device

합성예 1 ~ 26 및 111 ~ 114에서 합성한 화합물 Inv-1 ~ Inv-26및 Inv-111 ~ Inv-114올 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라녹색 유기 전계 발광소자를 제작하였다.  Compounds Inv-1 to Inv-26 and Inv-111 to Inv-114ol synthesized in Synthesis Examples 1 to 26 and 111 to 114 after performing high purity sublimation purification by a conventionally known method according to the following procedure Was produced.

먼저， IT0 (Indium tin oxide)가 1500A 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올， 아세톤, 메탄올 등의 용제로 초음파세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판올 5분간 세정하고 진공 증착기로 기판을 이송하였다.  First, IT0 (Indium tin oxide) was thin film coated glass substrate with a thickness of 1500A was washed with distilled water ultrasonic. After washing the distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, drying, transferring to a UV OZONE cleaner (Power sonic 405, Hwashin Tech) and washing the substrate for 5 minutes using UV and vacuum evaporator The substrate was transferred to.

이렇게 준비된 ITO투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ Inv-1 ~ M-MTDATA (60 nm) / TCTA (80 nm) / Inv-1 to the ITO transparent electrode thus prepared

Inv-26 및 Inv-111 ~ Inv-114의 각각의 화합물 + 10 % Ir(ppy)3 (300nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. Each compound of Inv-26 and Inv-111 to Inv-114 + 10% Ir (ppy) 3 (300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm The organic EL device was fabricated by laminating in order of).

[비교예 1] 유기 전계 발광소자의 제작 Comparative Example 1 Fabrication of Organic Electroluminescent Device

발광층 형성시 발광 호스트 물질로서 화합물 Inv-1 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.  A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Inv-1 when forming the emission layer.

상기 실시예 1~ 30및 비교예 1에서 사용된 m-MTDATA, TCTA, Ir(ppy)3, CBP및 BCP의 구조는 하기와 같다. The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP used in Examples 1 to 30 and Comparative Example 1 are as follows.

Figure imgf000263_0001
Figure imgf000263_0001

lr(ppy)3 lr (ppy) 3

[평가예] [Evaluation Example]

실시예 1-30 및 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/cuf에서의 구동전압， 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.  For each of the green organic electroluminescent devices fabricated in Examples 1-30 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cuf were measured, and the results are shown in Table 1 below. .

【표 1】  Table 1

Figure imgf000263_0002
Figure imgf000264_0001
Figure imgf000263_0002
Figure imgf000264_0001

Inv-111 ~ Inv— 114)을 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우 (실시 예 1-30) 종래 CBP를 사용한 녹색 유기 전계 발광 소자 (비교예 1)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있다.  Inv-111 to Inv— 114) as the light emitting layer of the green organic electroluminescent device (Example 1-30) in terms of efficiency and driving voltage compared with the green organic electroluminescent device using the CBP (Comparative Example 1) It can be seen that the better performance in the.

[실시예 31 - 114] 유기 전계 발광 소자의 제작 Example 31-114 Fabrication of Organic Electroluminescent Device

합성 예 27 ~ 110에서 합성한 화합물 Inv-27 ~ Inv-110을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 상기 실시 예 1과 동일한 방법으로 녹색 유기 전계 발광 소자를 제작하였다.  Compounds Inv-27 to Inv-110 synthesized in Synthesis Examples 27 to 110 were subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured in the same manner as in Example 1.

[평가예] [Evaluation Example]

실시 예 31 - 114 및 상기 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/crf에서의 구동전압， 전류효율 및 발광 피크를 측정하고， 그 결과를 하기 표 2에 나타내었다 . 【표 2】 Examples 31-114 and the driving voltage, current efficiency and emission peak at a current density of 10 mA / crf of each of the green organic electroluminescent devices fabricated in Comparative Example 1 were measured, and the results are shown in Table 2 below. It was. Table 2

Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000267_0001
Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000267_0001

녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우 (실시예 31ᅳ 114) 종래 CBP를 사용한 녹색 유기 전계 발광 소자 (비교예 1)와 비교해 볼 때 효율 및 구동전압 면에서 우수한성능을 나타내는 것을 알수 있다. When used as a light emitting layer of the green organic electroluminescent device (Example 31-114) When compared with the green organic electroluminescent device (Comparative Example 1) using the conventional CBP it can be seen that the excellent performance in terms of efficiency and driving voltage.

[실시예 115 212] 유기 전계 발광소자의 제작 Example 115 212 Fabrication of Organic Electroluminescent Device

합성예 115 ~ 212에서 합성한화합물 Inv-115 ~ Inv-212올통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.  Compounds Inv-115 to Inv-212 Synthesized in Synthesis Examples 115 to 212 After the high purity sublimation purification by a commonly known method, a red organic electroluminescent device was manufactured according to the following procedure.

먼저， ITO (Indium tin oxide)가 1500A 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코을, 아세톤， 메탄을 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405， 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.  First, a glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500A was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonically wash with isopropyl alcohol, acetone, methane, etc., dry it, transfer it to a UV ozone cleaner (Power sonic 405, Hwasin Tech), and wash the substrate using UV for 5 minutes and vacuum. The substrate was transferred to the evaporator.

이렇게 준비된 IT0투명 전극 위에 m-MTDATA (60 nm)/NPB (20 nm)/Inv-115 ~ M-MTDATA (60 nm) / NPB (20 nm) / Inv-115 ~ on the IT0 transparent electrode

Inv-212의 각각의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. Each compound of Inv-212 + 10% (piq) 2 Ir (acac) (30nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) An organic electroluminescent device was produced.

[비교예 2] 유기 전계 발광소자의 제작 Comparative Example 2 Fabrication of Organic Electroluminescent Device

발광층 형성시 발광 호스트 물질로서 화합물 Inv-115 대신 CBP를 사용하는 것을 제외하고는 실시예 115와 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다. A red organic electroluminescent device was manufactured in the same manner as in Example 115, except for using CBP instead of the compound Inv-115 as a light emitting host material when forming the light emitting layer. Produced.

상기 실시예 115 ~ 212및 비교예 2에서 사용된 m-MTDATA, NPB, (piq)2Ir(acac) CBP의 구조는 하기와 같다. The structures of m-MTDATA, NPB, and (piq) 2 Ir (acac) CBP used in Examples 115 to 212 and Comparative Example 2 are as follows.

Figure imgf000268_0001
Figure imgf000268_0001

m-MTDATA NPB  m-MTDATA NPB

[평가예]  [Evaluation Example]

실시예 115 ~ 212 및 비교예 2에서 제작한 각각의 적색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/cuf에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 3에 나타내었다.  For each of the red organic electroluminescent devices fabricated in Examples 115 to 212 and Comparative Example 2, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / cuf were measured, and the results are shown in Table 3 below. .

【표 3】  Table 3

Figure imgf000268_0002
Figure imgf000268_0002

Figure imgf000269_0001
Figure imgf000269_0001

Figure imgf000270_0001
Figure imgf000270_0001

[실시예 205 ~ 310] 유기 전계 발광 소자의 제작 합성 예 115 ~ 219에서 합성 한 화합물 Inv-115 ~ Inv-219을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 상기 실시예 1과 동일한 방법으로 녹색

Figure imgf000271_0001
전계 발광소자를 제작하였다. Examples 205 to 310 Fabrication of Organic Electroluminescent Devices Compounds Inv-115 to Inv-219 synthesized in Synthesis Examples 115 to 219 are commonly known. After high purity sublimation purification by the method
Figure imgf000271_0001
An electroluminescent device was manufactured.

[평가예] [Evaluation example]

실시예 205 ~ 310 및 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 10 mA/citf에서의 구동전압, 전류효율 및 발광 피크를 측정하고， 그 결과를 하기 표 4에 나타내었다.  For each of the green organic electroluminescent devices fabricated in Examples 205 to 310 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at a current density of 10 mA / citf were measured, and the results are shown in Table 4 below. .

【표 4】  Table 4

Figure imgf000271_0002
/// O-sosZSSMld 6εε£8020ζAV
Figure imgf000271_0002
/// O-sos Z SSM ld 6εε £ 8020 ζ AV

Figure imgf000272_0001
Figure imgf000272_0001

Figure imgf000273_0001
Figure imgf000273_0001

상기 표 3 및 표 4에 나타낸 바와 같이, 본 발명에 따른 화합물 (Inv-115 ~ Inv-219)을 적색 또는 녹색 유기 전계 발광 소자의 발광층으로 사용하였을 경우 (실시예 115 ~ 310) 종래 CBP를 사용한 적색 또는 녹색 유기 전계 발광 소자 (비교예 1 및 2)와 비교해 볼 때 효율 및 구동전압 면에서 보다 우수한 성능을 나타내는 것을 알수 있다. As shown in Table 3 and Table 4, when the compounds (Inv-115 ~ Inv-219) according to the present invention is used as a light emitting layer of the red or green organic electroluminescent device (Examples 115 to 310) using a conventional CBP Compared with red or green organic electroluminescent devices (Comparative Examples 1 and 2), better performance in terms of efficiency and driving voltage It can be seen that.

【산업상 이용가능성】  Industrial Applicability

본 발명의 화학식 1로 표시되는 인돌계 화합물은 우수한 내열성， 정공 주입 및 수송능, 전자주입 및 수송능， 발광능 등을 가지고 있어， 이를 정공 주입 /수송층, 전자 주입 /수송층 또는 발광층의 인광 /형광—호스트 /도판트 등으로 포함하는 유기 전계 발광 소자는 발광성능, 구동전압, 수명, 효율 등의 측면에서 크게 향상될 수 있어 풀 칼라 디스플레이 패널 등에 효과적으로 적용될 수 있다.  The indole-based compound represented by Formula 1 of the present invention has excellent heat resistance, hole injection and transporting ability, electron injection and transporting ability, light emitting ability, and the like. The organic electroluminescent device including a host / dopant can be greatly improved in terms of light emitting performance, driving voltage, lifespan, efficiency, etc., and thus can be effectively applied to a full color display panel.

Claims

【청구의 범위】 【청구항 1】 하기 화학식 1로 표시되는 화합물 : Claims Claim 1 Compound represented by the following formula (1): [화학식 1] [Formula 1]
Figure imgf000275_0001
상기 식에서， ¾ 및 R2는 각각 독립적으로 수소， 중수소， 할로겐， 시아노기， 니트로기， Cr o의 알킬기 , C3~C40의 시클로알킬기 , 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기 , 핵원자수 5 내지 60의 헤테로아릴기 , (：广(：40의 알킬옥시기， C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기， (：6 ~(：60의 아릴포스핀기， ( 6~(：60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되고，
Figure imgf000275_0001
Wherein, ¾ and R 2 are each independently hydrogen, deuterium, halogen, cyano, nitro, Cr o alkyl group, a C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group of the, C 6 ~ C 60 aryl group, a nuclear atoms aryl of from 5 to 60 heteroaryl group, (:广(: 40 alkyloxy of, C 6 ~ C 60 of the aryloxy group, C 3 ~ C 40 alkylsilyl group, C of 6 to C 60 arylsilyl group, C 2 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, (： 6 to (： 60 arylphosphine group, ( 6 to (： 60 aryl phosphate) It is selected from the group consisting of a pin oxide group and an arylamine group of C 6 ~ C 60 , 상기 Yi 내지 Y4 각각 독립적으로， N 또는 CR3이고， ^과 Y2 , Υ2와 Υ3 , 또는 Υ3와 Υ4 중 하나는 하기 화학식 2로 표시되는 축합 고리를 형성하며， The Yi to Y 4, each independently, it is N or CR 3, and one of Y and ^ 2, Υ Υ 2 and 3, or Υ Υ 3 and 4 forms a condensed ring represented by formula (2), [화학식 2]  [Formula 2]
Figure imgf000275_0002
상기 식에서， γ5 내지 Υ8은， 각각 독립적으로， Ν 또는 CR4이고， 점선은 상기 화학식 1의 화합물과 축합이 이루어지는 부위를 의미하며， 상기 )d 및 ¾는, 각각 독립적으로， 0， S, Se, N(Ar!), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되고, ¾및 ¾중 적어도 하나는 Ν(ΑΓι)이며， 상기 ¾및 R4는，각각독립적으로,수소，중수소，할로겐，시아노기，니트로기， (广(：40의 알킬기, C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， ~(：40의 알킬옥시기， C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기 , C2~C40의 알킬보론기， C6~C60의 아릴보론기, C6~C60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되고，
Figure imgf000275_0002
In the above formula, γ 5 to Υ 8 are each independently Ν or CR 4, and the dotted line means a site where condensation is made with the compound of Formula 1, D) and ¾ are each independently selected from the group consisting of 0, S, Se, N (Ar!), C (Ar 2 ) (Ar 3 ), and Si (Ar 4 ) (Ar 5 ), ¾ and is at least one Ν (Α Γι) of ¾, the ¾ and R4 are, each independently, hydrogen, deuterium, a halogen, a cyano group, a nitro group, (广(: 40 alkyl group, C of 3 ~ C 40 cycloalkyl Alkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, aryl jade having ~ (: 40 alkyloxy group, C 6 to C 60 group, C group 3 ~ C 40 alkylsilyl, C 6 ~ C aryl silyl group of 60, C 2 ~ C 40 group of an alkyl boron, C 6 ~ C group 60 arylboronic of, C 6 ~ aryl phosphine of C 60 A pin group, a C 6 -C 60 arylphosphine oxide group and a C 6 -C 60 arylamine group, 상기 A 내지 Ar5는, 각각 독립적으로， CrC40의 알킬기， C3~C40의 시클로알킬기, 핵원자수 3내지 40의 해테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d o의 알킬옥시기， C6~C60의 아릴옥시기, C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기 , C6~C60의 아릴포스핀기, C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되며， A to Ar 5 are each independently an alkyl group of CrC 40 , a cycloalkyl group of C 3 to C 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , or a nuclear atom of 5 To heteroaryl group of 60, alkyloxy group of do, aryloxy group of C 6 ~ C 60 , alkylsilyl group of C 3 ~ C 40 , arylsilyl group of C 6 ~ C 60 , C 2 ~ C 40 alkyl boron group, is selected from the aryl phosphine oxide group, and a C 6 ~ aryl group consisting of an amine group of the C 60 of the C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C 6 ~ C 60 of, 상기 ¾ 내지 및 A 내지 Ar5의 Cr o의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기, 핵원자수 5 내지 60의 헤테로아릴기， d- o의 알킬옥시기， (：6~(：60의 아릴옥시기 C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기, C6~C60의 아릴보론기， CS~C60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기는， 각각 독립적으로， 중수소, 할로겐， 시아노기， 니트로기, Cr o의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， Cr o의 알킬옥시기， C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 . 알킬보론기， C6~C60의 아릴보론기， C6~C60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 C«rC60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있다ᅳ The alkyl group of Cr o of ¾ to and A to Ar 5 , a cycloalkyl group of C 3 to C 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60, of 5 to 60 nuclear atoms Heteroaryl group, d-o alkyloxy group, (： 6 ~ (： 60 aryloxy group C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 2 ~ C 40 alkyl Boron group, C 6 ~ C 60 aryl boron group, C S ~ C 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and C 6 ~ C 60 arylamine group, each independently, , Halogen, cyano group, nitro group, Cr o alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, nuclear atoms 5 to 60 Heteroaryl group, Cr o alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 2 ~ C 40 . Alkyl boron group, C 6 ~ C group 60 arylboronic of, C 6 ~ C 60 aryl phosphine group, C aryl phosphine in 6 ~ C 60 pin oxide groups and C «with an aryl amine of rC 60 or more selected from the group consisting of May be substituted with a substituent 【청구항 2]  [Claim 2] 제 1항에 있어서 ,  The method of claim 1, 상기 화학식 1로 표시되는 화합물은 하기 화학식 la 내지 If로 표시되는 화합물로 구성된 군으로부터 선택되는 것을 특징으로 하는 화합물 :  Compound represented by Formula 1 is selected from the group consisting of compounds represented by the formula la to If: [화학식 la] [Formula la]
Figure imgf000277_0001
Figure imgf000277_0001
 [화학식 lb] [Formula lb]
Figure imgf000277_0002
Figure imgf000277_0002
 [화학식 lc]
Figure imgf000277_0003
[Formula lc]
Figure imgf000277_0003
 [화학식 Id] Formula Id
Figure imgf000278_0001
Figure imgf000278_0001
 상기 식에서， ， ， ， ¾ 및 Yi 내지 Y8은 제 1항에서 정의된 바와 같다 . Wherein,,,, ¾ and Yi to Y 8 are as defined in claim 1. 【청구항 3】 [Claim 3] 제 1항에 있어서，  The method of claim 1, 상기 A 내지 Ar5는，각각 독립적으로， C6~C60의 아릴기，핵원자수 5 내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 것을 특징으로 하는 화합물 . A to Ar 5 , each independently, a C 6 ~ C 60 An aryl group, a nuclear atom of 5 to 60 heteroaryl group and C 6 ~ C 60 An arylamine group characterized in that the compound selected from the group consisting of . 【청구항 4】  [Claim 4] 제 1항에 있어서， 상기 ¾ 내지 ¾는 , 각각 독립적으로， C6~C60의 아릴기， 핵원자수 5 내지 60의 해테로아릴기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 것을 특징으로 하는 화합물 . The method of claim 1, The ¾ to ¾ are each independently selected from the group consisting of C 6 ~ C 60 aryl group, nuclear hetero atoms 5 to 60 heteroaryl group and C 6 ~ C 60 arylamine group . 【청구항 51  [Claim 51] 제 1항에 있어서，  The method of claim 1, 상기 및 ¾는 모두 N(An)인 것을 특징으로 하는 화합물 .  And ¾ are both N (An). 【청구항 6】  [Claim 6] 제 5항에 있어서，  The method of claim 5, 상기 화학식 1로 표시되는 화합물은 하기 화학식 3으로 표시되는 화합물인 것을 특징으로 하는 화합물 .  Compound represented by the formula (1) is a compound characterized in that the compound represented by the formula (3). [화학식 3]  [Formula 3]
Figure imgf000279_0001
Figure imgf000279_0001
 상기 식에서， ， ¾ 및 내지 丫4는 제 1항에서 정의된 바와 같으며， ^과 Υ: Υ2와 Υ3 , 또는 Υ3와 Υ4 증 하나는 하기 화학식 4로 표시되는 축합 고리를 형성하며，Wherein R,, ¾ and to丫4 are as defined in claim 1, ^ and Υ: Υ 2 and Υ 3, or Υ 3 and Υ 4 increases one to form a condensed ring represented by formula (4), and ， [화학식 4]
Figure imgf000280_0001
상기 식에서， Υ5 내지 Υ8은 제 1항에서 정의된 바와 같으며， 점선은 상기 화학식 3의 화합물과 축합이 이루어지는 부위를 의미하고， [Formula 4]
Figure imgf000280_0001
In the above formula, Υ 5 to Υ 8 are as defined in claim 1, the dotted line means a site where the condensation is made with the compound of Formula 3, 상기 은 C6~C60의 아릴기 또는 핵원자수 5 내지 60의 헤테로아릴기이고， 상기 Ra및 ¾는,각각독립적으로 수소, 중수소，할로겐， 시아노기 , 니트로기，The C 6 ~ C 60 An aryl group or a heteroaryl group of 5 to 60 nuclear atoms, wherein R a and ¾ are each independently hydrogen, deuterium, halogen, cyano group, nitro group, <广(：40의 알킬기， ~(：40의 시클로알킬기， 핵원자수 3 내지 40의 해테로시클로알킬기， C6~C60의 아릴기 핵원자수 5 내지 60의 해테로아릴기， d— o의 알킬옥시기 C6~C60의 아릴옥시기 C3~C40의 알킬실릴기, C6~C60의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기， C6~C60의 아릴포스핀기 rC60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되며, <广 (： 40 alkyl group, ~ (: 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, aryl group having 6 to C 60 atoms, heteroaryl group having 5 to 60 nuclear atoms, d— o alkyloxy group of C 6 ~ C 60 aryloxy group C 3 ~ C 40 alkylsilyl group, C 6 ~ C 60 arylsilyl group, C 2 ~ C 40 alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 aryl phosphine group rC 60 is selected from the group consisting of aryl phosphine oxide group and C 6 ~ C 60 arylamine group, 상기 Ra 및 ¾의 C广 C40의 알킬기, C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 헤테로시클로알킬기, C6~C60의 아릴기， 핵원자수 5 내지 60의 해테로아릴기， C C40^ 알킬옥시기, C6~C6(^ 아릴옥시기， C3~C40의 알킬실릴기， (：6~(60의 아릴실릴기， C2~C40의 알킬보론기， C6~C60의 아릴보론기， (：6~(：60의 아릴포스핀기， C6~C60의 아릴포스핀옥사이드기 및 (：6~(:60의 아릴아민기는, 각각 독립적으로， 중수소， 할로겐, 시아노기， 니트로기， Cr o의 알킬기， QrC40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d- o의 알킬옥시기 , C6~C60의 아릴옥시기， C3~C40의 알킬실릴기， C6~C60의 아릴실릴기， C2~C40의 알킬보론기， CfrC60의 아릴보론기 , CfrC60의 아릴포스핀기， (VC60의 아릴포스핀옥사이드기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택된 하나 이상의 치환기로 치환될 수 있으며， The C a C 40 alkyl group of C a and ¾, a C 3 -C 40 cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , a solution of 5 to 60 nuclear atoms Teroaryl group, CC 40 ^ alkyloxy group, C 6 ~ C 6 ( ^ aryloxy group, C 3 ~ C 40 alkylsilyl group, (： 6 ~ ( 60 arylsilyl group, C 2 ~ C 40 alkyl Boron group, C 6 to C 60 aryl boron group, (: 6 to (: 60 aryl phosphine group, C 6 to C 60 aryl phosphine oxide group and (: 6 to (: 60 aryl amine group, respectively) Independently, deuterium, halogen, cyano group, nitro group, Cr o alkyl group, QrC 40 cycloalkyl group, nuclear atom of 3 to 40 Heterocycloalkyl group, C 6 ~ C 60 Aryl group, Nuclear 5 to 60 heteroaryl group, d-o alkyloxy group, C 6 ~ C 60 Aryloxy group, C 3 ~ C 40 Alkylsilyl Group, C 6 ~ C 60 arylsilyl group, C 2 ~ C 40 alkyl boron group, C f r C 60 aryl boron group, CfrC 60 aryl phosphine group, (aryl phosphine oxide group of VC 60 and C 6 It may be substituted with one or more substituents selected from the group consisting of arylamine groups of ~ C 60 , 상기 n 및 m은， 각각 독립적으로， 0 내지 5의 정수이고， 단 n+m은 적어도 1 이상이다.  N and m are each independently an integer of 0 to 5, provided that n + m is at least one. 【청구항 7】  [Claim 7] 제 5항에 있어서 ,  The method of claim 5, 상기 화학식 1로 표시되는 화합물은 하기 화학식 5으로 표시되는 화합물인 것을 특징으로 하는 화합물 :  Compound represented by the formula (1) is a compound characterized in that the compound represented by the formula (5): [화학식 5]  [Formula 5]
Figure imgf000281_0001
상기 식에서 , ， R2 및 ^ 내지 Y4는 제 1항에서 정의된 바와 같으며， Y Y2 , Υ3, 또는 Υ3와 Υ4 중 하나는 하기 화학식 6으로 표시되는 축합 고리를 형성하고， [화학식 6]
Figure imgf000281_0001
Wherein, R 2 and ^ to Y4 are as defined in claim 1 , YY 2 , Υ 3 , or one of Υ 3 and Υ 4 to form a condensed ring represented by the following formula (6), 6]
Figure imgf000282_0001
Figure imgf000282_0001
 상기 식에서 , Y5 내지 Υ8은 제 1항에서 정의된 바와 같으며， 점선은 상기 화학식 5의 화합물과 축합이 이투어지는 부위를 의미하고， Wherein, Y 5 to 5 8 are as defined in claim 1, and the dotted line means a site where condensation occurs with the compound of Formula 5, 상기 내지 Ζ6은， 각각 독립적으로 , Ν 또는 CAr6이며， To Ζ 6 are each independently Ν or CAr 6 , 상기 Ar6 , A 및 B 는，각각 독립적으로， C广 C40의 알킬기， C3~C40의 시클로알킬기， 핵원자수 3 내지 40의 해테로시클로알킬기， C6~C60의 아릴기， 핵원자수 5 내지 60의 헤테로아릴기， d~C40의 알킬옥시기， C6~C60의 아릴옥시기， C3~C40의 알킬실릴기 , C6~C60의 아릴실릴기 , C2~C40의 알킬보론기， (：6~(：60의 아릴보론기， (：6~(：60의 아릴포스핀기 , C6~C60의 아릴포스핀옥사이드기 및 CfrC60의 아릴아민기로 구성된 군으로부터 선택되고， Ar 6 , A and B, each independently, an alkyl group of C 广 C 40 , a cycloalkyl group of C 3 to C 40 , a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 60 , Heteroaryl group having 5 to 60 nuclear atoms, d-C 40 alkyloxy group, C 6 -C 60 aryloxy group, C 3 -C 40 alkylsilyl group, C 6 -C 60 arylsilyl group, C 2 ~ C 40 alkyl boron group, (： 6 ~ (： 60 aryl boron group, (： 6 ~ (： 60 aryl phosphine group, C 6 ~ C 60 aryl phosphine oxide group and C f r C 60 Is selected from the group consisting of arylamine groups, 상기 r 및 s는 각각 0 내지 5의 정수이고， 단 r+s는 적어도 1 이상이며， 상기 p 및 q는 각각 0 내지 3의 정수이다 .  R and s are each an integer of 0 to 5, provided that r + s is at least 1, and p and q are each an integer of 0 to 3, respectively. 【청구항 8】  [Claim 8] 제 7항에 있어서，  The method of claim 7, 상기 화학식 5로 표시되는 화합물은 하기 화학식 5a 내지 5f로 표시되는 화합물로 구성된 군으로부터 선택되는 것올 특징으로 하는 화합물 : Compound represented by the formula (5) is represented by the formulas 5a to 5f Compounds characterized by being selected from the group consisting of compounds: [화학식 5a]
Figure imgf000283_0001
[Formula 5a]
Figure imgf000283_0001
 [화학식 5b] [Formula 5b]
Figure imgf000283_0002
Figure imgf000283_0002
 [화학식 5c] [Formula 5c]
Figure imgf000284_0001
Figure imgf000284_0001
 [화학식
Figure imgf000284_0002
Formula
Figure imgf000284_0002
 [화학식 5e]
Figure imgf000284_0003
Figure imgf000285_0001
상기 식에서， ， ， Υι내지 Y8, Ζχ내지 ， A, Β, rᅳ s, ρ 및 q는 제 7항에서 정의된 바와 같다. [Formula 5e]
Figure imgf000284_0003
Figure imgf000285_0001
In the above formula, ， Υι to Y 8 , Ζ χ to, A, Β, r ᅳ s, ρ and q are as defined in claim 7. 【청구항 9】  [Claim 9] 제 7항에 있어서，  The method of claim 7, 상기 Ar6, A및 B는， 각각독립적으로, C6~C60의 아릴기， 핵원자수 5내지 60의 헤테로아릴기 및 C6~C60의 아릴아민기로 구성된 군으로부터 선택되는 것을 특징으로 하는 화합물. Wherein Ar 6, A and B are, each independently being selected from C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, and a C 6 ~ C 60 aryl group consisting of an amine group of Compound. 【청구항 10】  [Claim 10] 제 1항에 있어서，  The method of claim 1, 상기 ^이 S일 때 ¾는 N r 이고， ¾가 S일 때 )^는 N i^ J 것을 특징으로 하는 화합물 .  Wherein when ¾ is S, ¾ is N r, and when ¾ is S, ^ is N i ^ J. 【청구항 11】  [Claim 11] 제 10항에 있어서，  The method of claim 10, 상기 화학식 1로 표시되는 화합물은 하기 화학식 6a 내지 61로 표시되는 화합물로 구성된 군으로부터 선택되는 것을
Figure imgf000286_0001
Compound represented by Formula 1 is represented by the following formula 6a to 61 Selected from the group consisting of compounds
Figure imgf000286_0001
 [화학식 6a][Formula 6a]
Figure imgf000286_0002
Figure imgf000286_0002
 [화학식 6b] [Formula 6b]
Figure imgf000286_0003
Figure imgf000286_0003
 [화학식 6c]
Figure imgf000286_0004
[Formula 6c]
Figure imgf000286_0004
 [화학식 6e] [Formula 6e]
Figure imgf000287_0001
Figure imgf000287_0001
 [화학식 6i] [Formula 6i]
Figure imgf000288_0001
Figure imgf000288_0001
 [화학식 6k] [Formula 6k]
Figure imgf000288_0002
Figure imgf000288_0002
 상기 식에서， ， ， Yi 내지 Ys 및 A 은 제 1항에서 정의된 바와 같다. In the above formula, ， Yi to Y s and A are as defined in claim 1. 【청구항 12] [Claim 12] (i) 양극， (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재 (介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광소자로서，  An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode, 상기 유기물층 중에서 적어도 하나는 제 1항 내지 제 11항 증 어느 한 항에 따른 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광소자.  At least one of the organic material layer comprises an organic electroluminescent device comprising the compound according to any one of claims 1 to 11. 【창구항 13】  [Wind port 13] 제 12항에 있어서，  The method of claim 12, 상기 화합물을 포함하는 유기물층은 정공 주입층， 정공 수송층， 전자 주입층， 전자 수송층 및 발광층으로 구성된 군으로부터 선택되는 것을 특징으로 하는 유기 전계 발광소자.  The organic material layer comprising the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer and a light emitting layer. 【청구항 14】  [Claim 14] 제 12항에 있어서，  The method of claim 12, 상기 화합물은 발광층의 인광 호스트로 사용되는 것을 특징으로 하는 유기 전계 발광 소자. The compound is an organic EL device, characterized in that used as a phosphorescent host of the light emitting layer.
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